


Craving You

by turningthepages



Series: Craving You [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Best Friends, Bottom Castiel (Supernatural), Coming Out, Dorms, Falling In Love, First Time, Fluff, Fluff and Angst, Fluff and Smut, Friends With Benefits, Friendship, Idiots in Love, M/M, Mutual Pining, Pining, References to Depression, Roommates, Self Confidence Issues, Slow Burn, Top Dean Winchester
Language: English
Status: Completed
Published: 2019-10-14
Updated: 2020-03-22
Packaged: 2020-12-14 22:03:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 19
Words: 112,793
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21022961
Author URL: https://archiveofourown.org/users/turningthepages/pseuds/turningthepages
Summary: Castiel Milton: Twenty-one years young, college senior, Romance Languages major, and virgin.After a night at a party where things did not go quite as he'd hoped, Castiel is determined to never again be a shy, nervous, newbie to hookups. With there only being one person in his life he trusts enough to help him navigate all this, Castiel asks his best friend and roommate, Dean, to help him out.





	1. September 17, 2017

**Author's Note:**

> First things first, this is my first ever explicit work. I'm nervous. We'll power through. (Smut will begin chapter 2) 
> 
> Secondly, I've been working on this story for nearly 2 years now, I have 14/19 (maybe 20) chapters completely written and I will be updating this fic each weekend until I catch up to what I have finished. So far this work is upwards of 80k, so chapters will be quite long for the most part. 
> 
> Enjoy :)

College seemed to follow a steady routine:

Ramen 

Pizza

Parties 

Tequila 

Tacos (Tuesdays)

More tequila

Sometimes sleep

It was difficult to put into words the mixed feelings he had on his time at university so far, but despite the weirdness, Castiel Milton knew he was enjoying himself. He’d given the campus clubs a try. He’d given a few joints a try. He’d eaten his fair share of college-approved foods, and had put on that inevitable “freshman fifteen.” He’d definitely even given the nightlife a try, or continuous tries since he was now three years into his degree and still found himself going out every so often with his friends. 

College wasn’t exactly what he’d pictured it to be. All throughout his schooling his teachers had ranted and raved about college being the most prestigious time of his life yet here he was, taking courses from professors who taught strictly based on memes. Yes, there was a level of prestige that went with being at a university, but sometimes that prestige faded when he saw the masses coming to school dressed in pajamas. 

He liked his school though, the University of Nevada, even if he didn’t look the type that’d want to live Las Vegas. But something about the place made him excited. It wasn’t like his college was located directly on the bustling strip, surrounded by hotels and casinos but it did bring a certain atmosphere that he believed other universities wouldn’t be able to offer. 

When driving over from California to move into the dorms, Castiel had been optimistic about his time away at college. He hoped that starting fresh in a new environment would break him out of the shell he’d been living in and that he’d be forced into more social events because he had no other choice but to get out there and make friends. Most of all he’d silently hoped that he’d at least be able to befriend his roommate. They’d been matched online but Castiel had been too nervous to reply back to the welcoming email he’d received from the other boy. 

To his relief, he _was_ paired with a roommate he clicked with. From the moment he’d stepped into the room, Dean Winchester was a solid part of Castiel’s life. His boisterous voice, sturdy handshake, and confident posture had drawn Castiel and all his shyness in like a moth to a flame. 

Dean had introduced himself to Castiel as a self-proclaimed “geek with an unhealthy obsession with my car and if you can’t get on board with that, we should probably request a transfer now.” Needless to say, Cas stayed. (He loved Dean’s ‘67 Chevy Impala and all the ‘nerdy’ things Dean was into). 

They’d been roommates for three years now, choosing to stay in the dorms since Dean had a full ride to the University, housing included, and Castiel couldn’t imagine living with anyone other than the green-eyed man. 

He liked his life on campus and it helped that he had his best friend (aside from Dean) Hannah living so close too. 

She and Castiel had gone to high school together and then subsequently the same university though they’d never actually talked in high school. Despite that, they grew extremely close during the first few weeks of college when they only had each other. Now they thought of each other as family, which is why Castiel didn’t feel so shitty as he woke up that morning laying on a hard, unforgiving surface. 

For a brief, panicked moment he suspected he’d fallen asleep somewhere embarrassing—like the room of the guy he’d attempted to go home with the night prior, but when he inhaled the familiar scent of warm vanilla sugar, he knew with certainty that he’d bothered Hannah into letting him crash on her floor instead of having to explain to Dean why he was such a mess the night before. 

Even the events from the night before were a bit of a mess in Castiel’s mind. He hated nights when he got as plastered as he did because the mornings after were always the worst. He _usually_ didn’t drink enough to wake up dehydrated and bordering on liver failure. He _usually_ just spent the nights dragging his sloppy drunk friends back to their dorms, cleaning them up, and tucking them in before making his way back to his dorm to then only get a few hours of sleep before the room filled with god-awful amounts of sunshine…. 

Usually. 

Last night he’d been on a mission of sorts. It was embarrassing to even think about now how hard he’d convinced himself it was a good idea. How he’d had to encourage himself (repeatedly) that he did indeed need one more shot of liquid courage—why’d he go with tequila? 

He really wanted to pretend that last night hadn’t happen. Or more so that it hadn’t ended the way that it had. First steps in pretending it didn’t happen was to avoid talking about what did happen. 

The sunlight that currently hit his face with an unforgivable brightness was enough to tell him that it was only a matter of minutes that Hannah would be waking up and forcing him to spill. He weighed the pros and cons of actually facing her questioning or going back to his own room. With leaden arms he groped around for his phone and held it close to his face to reveal the time. He’d be pushing it but he figured with the blackout curtains Dean insisted on having and the fact that it was about an hour before Dean usually woke up on the weekends, it would be safe for Cas to slip back into their room and sleep for the rest of the day, unquestioned by his even nosier best friend. 

When Castiel pulled himself upright from the ground he gazed over to his friends’ bed seeing her fast asleep. Not wanting to wake her up, he quietly pulled himself off the floor and made his way to the front door. 

He made it back to his and Dean’s room in merely ten minutes, smiling when he heard his best friend’s dead-asleep snores. It meant he didn’t have to talk about any of the events last night and his feelings on said events. Without much preamble he shoved off all of his clothes until he was down to his boxers and nearly nose-dived into his bed, sighing happily at the feeling of his cool sheets on his aching body. He was dead to the world in a matter of seconds. 

When Castiel awoke it was to the sound of video games on a low volume and the glow of the television screen in their dark room. Dean was always courteous about not waking Cas when he was sleeping—Castiel was inherently not a morning person. 

Quelling his rolling stomach and pounding head, he laid in bed listening to the sound of gunfire from the speakers, knowing Dean was without a doubt playing one of the old Call of Duty’s in preparation for the newer one coming out soon. 

It was out of no other desire than to not be a bum in bed all Sunday that he slipped off of his bed, pulling his blanket with him, and plopped down into the beanbag chair beside his best friend on the futon. Because Dean was a righteous and thoughtful man, the lights in their room stayed off and the volume of the game stayed low. 

Dean was pretty adamant that Sundays be spent strictly bumming around in boxers and eating cold leftovers on their futon while watching an entire Netflix series in one shot. It was the one day of the week that Dean never let anyone over to the dorm, unless that someone were his younger brother Sam or Hannah, and it just stayed the two of them all day. Despite trying to tell himself that it wasn’t his favorite day of the week, it was definitely Cas’s favorite day of the week. He’d always anxiously look forward to having Dean all to himself, just comfortably in each other’s presence. 

It’d felt like that for Castiel for as long as he could remember. From their first weekend together, awkwardly eating Panda Express on their newly purchased futon, fumbling over which questions were appropriate to ask each other in their newfound friendship—Castiel had felt completely at ease in Dean’s presence. Dean was just one of those people that others wanted to be around and Castiel would probably always remain at the top of that list. 

He looked away from the television screen for a moment to peer over at the man in question. Dean was already staring at him in return; the game now paused on the screen. He didn’t say anything, just looked Castiel over before he pulled out his phone and pressed a few buttons before pulling it to his ear. 

“I’d like to place an order for delivery.” _Oh bless his soul_ Castiel thought, feeling his stomach rumble. He loved that he and Dean didn’t even have to speak to communicate anymore. But what literal pile of garbage did Castiel currently look for Dean to jump straight to caretaker mode? 

“Yes—my name is Dean. Oh you remember me? Awesome.” Cas laughed at Dean’s conversation with the hostess. It was perhaps a bit of a problem that certain restaurants knew them by name now… Maybe he and Dean did eat out a little too often. It still didn’t stop them from ordering takeout though. 

“Yup, that sounds right. Pad Thai, Broccoli Beef, and four egg rolls.” There was another short pause in Dean’s phone call as he likely heard the total for the food. 

“Cool. Thanks.” Dean muttered before hanging up. 

From the cocoon of blankets he’d somehow knotted himself in, Castiel croaked out a pathetic, “I worship the ground you walk on.” 

His voice was rougher than normal. What he wouldn’t give for some sort of mojo to zap a water bottle into his hand whenever he needed. 

“Here. Water.” 

Silently thanking all Gods for making Dean the most wondrous human to ever walk planet earth, Castiel greedily reached for the bottled water his roommate offered him. “You’re too good to me.” 

“I know. I should request a transfer, find someone who doesn’t need to be constantly taken care of.” 

Dean smiled over at Cas with amusement. He always seemed to enjoy the mornings that Castiel was the most hung-over, much to Cas’s chagrin and this morning seemed to be no exception. Castiel must have really looked like hell this particular morning if the devious smirk covering his best friend’s face was anything to go by. It wasn’t fair though. Castiel always looked like shit in the morning and he just so happened to look like burnt shit the mornings after drinking. Dean however had a tendency to still look like a male model no matter how he woke. The only way the tanned, freckled faced man ever showed signs of being a little bit hung over in the mornings was his hair being pressed against his face in odd angles. It wasn’t fair. 

So, Cas tried to bring him down to his peasant level. 

“I cleaned up your puke not even two weeks ago. It was blue and had chunks.” Cas deadpanned, narrowing his eyes in playful contempt until Dean cracked an even wider smile. 

“Fine! I’ll keep you.” 

Humming noncommittally, Castiel snuggled back down into his spot, pulling the blanket around his head. He was smiling ear to ear but he knew by the placement of his blanket that Dean wouldn’t be able to see it.

“Stop talking now.” Cas mumbled from his little nest, because he knew his pretend sassiness never failed to make Dean smile. 

“Love ya too, buddy.” 

Cas watched Dean play through more of the video game’s campaign, neither man bothering to make any small talk. Even when the food arrived they silently went about the space finding what few clean silverware they had and sat back down in their spots to eat. Before long they were stuffed (though they’d probably be hungry in another hour or so) and content to just stay in each other’s presence not needing to fill it with idle chatter. 

Cas liked that he got to be around this side of Dean when very few others could. Dean always found himself leading conversations, staying animated and lively to make sure no one was left out in social gatherings. He’d go round and round talking to everyone and making them laugh, never leaving room for silence. It was something Dean felt compelled to do, he’d once told Castiel, because if Dean could steer conversation then it meant no one could ask him too many questions and that meant not needing to divulge parts of his past he’d rather leave unsaid. 

He’d told Castiel about it all roughly six months into their friendship, opening up to him in a way he hadn’t with many other friends. He’d described growing up with his younger brother Sam and being forced to raise him after their mother had been killed by a drunk driver when Dean was only four. He’d told Cas about his father’s anger problems, taking it out on both the young boys until Dean was six and a social worker took them away after Dean’s teacher asked about his bruises. 

Dean told him about growing up with Jody and later Bobby who loved and cared for Dean and Sam, setting them up on their path of success. But he’d also told Cas of the few and far between visits with his biological father, the man having flittered in and out of rehab later to die at the hand of his vice. It made sense why Dean didn’t want to share his origins and Castiel respected his privacy, never breathing a word of the life young Dean had lived, even to their closest friends. 

Dean was a great man, even though he seemed to think otherwise. He was kind and thoughtful, never asking for anything of anyone. Castiel knew he could trust Dean with anything, and knew that if he asked for something within reason Dean would follow through. Castiel trusted him completely. Over and over he’d tell Cas that he was family and those words… they meant more to Cas than he knew how to explain since he didn’t have much in the way of family. Biological family that is. 

He knew Gabriel wasn’t his biological father. He knew that technically Gabriel was his uncle and that his mother Anna had been diagnosed with terminal cancer when she was still pregnant with him. He knew that Gabriel had never wanted children but when Anna entrusted Castiel over to him in her will Gabriel refused to hear of another one of his siblings raising the baby. Castiel also knew that the doubt Gabriel’s siblings placed on his ability to effectively raise Castiel was what led Gabriel to cutting off his family and creating a smaller unit with just the two of them. 

Castiel knows Gabriel isn’t his father but he thinks of him as such and refers to him as such. Maybe his parenting choices weren’t always the greatest. Perhaps Castiel had a few too many cavities growing up since Gabriel didn’t seem to understand that ice cream and other sweets were not in fact a part of the food pyramid. It was possible that Castiel had seen a few more scantily dressed women walking shamefully out their front door than other kids saw growing up. And yeah, the advice Gabriel gave him some of the time was a little dodgy but he did his best. Never once did Castiel go hungry. Never once did Gabriel say that he didn’t have time to work on homework with him or take him to the park. 

Gabriel showed up to every parent teacher conference and he sat second row for every school performance. He hung up all of Cas’s artwork on the refrigerator and kept every single memento Castiel ever made in school. Even now Gabriel checks on Cas every day and calls him on Thursdays just to hear his voice. Castiel loves him immensely and loves that it had just been the two of them against the world all his life. It has just made him happier to grow his family, person by person. Now he has Hannah and Dean (and Dean’s brother Sam) as part of the people he can call his family too. 

Suddenly pulled from his thoughts, Castiel found himself having to use more energy than he currently possessed to sift through his blankets in order to pull out his phone that had just buzzed three times. 

Speaking of family. 

**Hannah:** Are you all right, Castiel? 

**Hannah:** Please tell me that you’re alright. I’ve been worried about you all morning. You were more upset last night than I’ve ever seen you but you wouldn’t tell me why.

**Hannah:** If I don’t hear from you in five minutes I’m going to message Dean. 

_Cas:_ I’m alright. I’ll tell you later, I promise. 

**Hannah:** I understand. 

Castiel really didn’t want to talk about last night. It was more out of sheer embarrassment that he just wanted everything that had happened last night to go away. He’d made a complete idiot out of himself, not to mention he’d been completely plastered. He wishes he could blame it on Balthazar but really it was Castiel’s own damn fault that he’d gone out. 

He’d just been… itching lately for… something. Every day he just found himself wanting and wanting… wanting things he’d never had before. He was twenty-one years old and… 

God damnit. He was twenty-one years old and he was a virgin to boot. 

It’s not that he was saving himself. That was never the case. He just… he never had an opportunity. He’d been shy growing up and had never known many people, let alone met anyone who had been mutually interested in dating. The years just ticked by and he kept on being a virgin. There really wasn’t anything he could do about it. 

But lord, have mercy, did he want to. 

He craved touch, just as he figured most of the population does. He found himself fantasizing more and more about how it would feel… how it would be… how everyone seemed to be so driven by such a carnal act. Why was he still missing out on something that brought so many people such pleasure? 

He wanted to change that. 

He wanted to change it so badly but he just didn’t know how. So when one of his friends, Balthazar, had said “frat party” Castiel’s downstairs brain had taken control. Little Cas thought of it as the perfect opportunity to get what it wanted and what a fucking mistake that had been. 

To be outright denied on his first and only attempt at sexual conduct was more mortifying than Castiel had ever imagined it would be. 

A thick, heavy knot still settled in his stomach and he knew it wasn’t from the hangover. He wanted to fix this. He wanted to never have to go through a night like that again… walking back to his friend’s dorm with snotty, drunken tears rolling down his face as he realized just how undesirable he really was. 

No. Next time he tried to hook up with someone he’d know what he was doing. He would never again embarrass himself with awkward virginal fumbling. He wanted to be the type of person that partners came crawling back for… that craved him in ways he didn’t know possible. He wanted someone to be driven mad with desire for him. 

But he had to learn how to be desirable first. He had to learn the right ways to please someone before he could leave them wanting for more. 

He just didn’t know how….

He needed someone to teach him. But where was he going to find someone like that? His first thoughts went to a strip club… but… he didn’t have the money for that. And dear lord, he’d been watching porn for years and that clearly did not help him in the slightest if last night were anything to go by. Ideally, he’d just go to another party and find a random person but…. He wasn’t going to make that mistake again. 

It needed to be someone who wouldn’t judge him for being a virgin or make him feel like an idiot for wanting to learn how to give pleasure. It needed to be someone he trusted… How was he going to find someone like that? 

He found himself asking one of the two people he could ask for advice about this. 

“Dean?” 

“It lives!” His best friend exclaimed loudly, like the obnoxious butthead he could be. Castiel threw the blanket that was beginning to suffocate him onto the floor and sat upright on the beanbag chair. 

“I hate you.”

Dean just smiled. “I know. What’s up?” 

He was still playing his video game cussing at the screen each time he was killed by an enemy. And as his friend played, Castiel wondered if he should even interrupt him. Were his problems even that important? He figured the safest person to ask would be Dean. He wasn’t exactly open about his sex life but Castiel knew he had one… surely his friend would be able to steer him in the right direction. 

“Can we talk?” 

“Uh? Yeah?” Dean quickly paused the game and threw his controller aside, seeming to sense the uncertainty in Cas’s voice. 

“You… you know how I went out last night… to Mick’s party…” 

Tension formed between Dean’s eyebrows as he nodded to Castiel’s question. “Yeah? Did something happen?” 

“Well, kind of. I met a guy.” 

“Yeah?” 

“But… it didn’t end well.” 

Dean’s face paled. He was concerned. “What do you mean?” 

“Uh—Arthur, his name is Arthur, and I had been talking which lead to you know… kissing. Oh and he’s Mick’s roommate by the way.” Castiel knew he was doing a shit job of explaining himself, as Dean’s face seemed to grow more worried. Still Castiel trudged on trying to be thorough. “So uhm… after a while he invited me back to his room…” 

“Look at me.” 

Cas’s eyes snapped up to Dean’s. His roommate’s green eyes were burning into him. “What?” Castiel asked in concern. 

“Did he lay a hand on you?” 

“What?” He could feel Dean’s eyes searching and scanning all over him, looking for something. 

“I swear to God if he forced you to do anything you didn’t want—”

“No! No!” Cas threw his hands out and gripped his friend’s forearm. “Oh, Dean. I’m sorry. No it was nothing like that. I swear.” 

Dean looked him over a few moments more, not exactly satisfied that Castiel was telling the truth. “Okay,” he said when he seemed to calm down a touch. “Go on.” 

“So we were going to his room with the intent of, you know…” 

Realization dawned on him and Dean’s face suddenly contorted into a grimace. “Oh! Dude, I don’t need to know about your sexcapades.” 

“—And things were getting more heated.” Castiel tried to proceed. If he didn’t explain his dilemma to Dean now, he probably never would. 

“Dude!” 

Dean tried to flop back against the couch and grab for his controller. It made Castiel suddenly feel panicky. If Dean wouldn’t listen to him about this then who could Cas tell? 

“Dean, please! I have a point.” 

His friend looked over at him and glared. It seemed to be more out of discomfort than him genuinely not wanting to hear what Castiel had to say but left Cas feeling nervous all the same. Maybe it was something in Cas’s face that suddenly made Dean drop his putout facade. 

“I’m listening. I promise.” 

“So, things were getting more heated and we were undressing each other and I knelt down to pull his pants down—“ 

“Ugh!” 

“Dean you said you’d listen!” Castiel felt himself blushing. It was hard enough to be telling this to his roommate but it was even harder having to start and stop. 

“I am! I am listening!” 

“Please don’t interrupt anymore,” he pleaded before continuing… staring at a nondescript part of their floor to get the next part out. “As I was pulling his pants down, I guess my nerves got the best of me because I mentioned that I’d ‘never done this before’ and—and he made me stop.” 

Cas’s heart was pounding in his chest reliving what’d happened. He’d been so nervous walking back to Arthur’s room. None of the shots he’d taken had calmed them either and he found himself shaking in his boots as he tried to pretend like he wasn’t a complete newbie to the whole sex scene. It was honestly probably the tequila that made him word vomit that he’d never done anything like that before… that he’d never done this before… that he was nervous that he wouldn’t be that good. 

The look on Arthur’s face… 

“Well that’s good,” Dean cut into his thoughts; “he didn’t want to push you to something you might not have been ready for.” 

Castiel huffed in frustration. He wished that were the case. “No… I don’t believe that was his intent. His words were ‘what, are you a fucking virgin?’ and when I confirmed that I was… he uh—he told me to put my clothes back on.”

“What?” Dean asked, confused. 

“And—and as I was getting dressed again he told me that I should have warned him because ‘people don’t want to fuck a virgin, they just get too clingy and too many feelings get involved’ but he did say he’d be interested sometime in the future if I got more experience.” 

God, even just saying it out loud made the burning embarrassment come back full force. He’d been down on his fucking knees with another man’s dick in his hand. Fuck… he’d even been about to put it in his mouth and then he was rejected? Just because he said he’d never done it before? Was he really that undesirable that Arthur didn’t even want him to try? Didn’t guys like getting sucked even if it was only mediocre at best? God, even thinking back to the night Cas was now almost positive Arthur hadn’t even been fully hard. 

Mortifying. 

It was honestly so mortifying. And now Dean had heard the story. 

“I’ll tell you right now that’s not fucking happening.” Dean exclaimed, fuming. He looked ready to march over to the other man’s house and deck him in the face. “Asshole lost his shot with you!” 

“No, no, I agree with you.” Castiel said softly. “I wouldn’t want to pursue a sexual relationship after his rejection anyway.” 

“Good! You shouldn’t! You’re way too fucking good for that. What a fucking prick!” The anger in Dean’s voice settled something in Cas. The fact that Dean was so protective was definitely comforting. 

Castiel’s mind went back to the first time Dean had ever brought out his protective side. They’d been at a party, as all of Cas’s embarrassing stories seem to start. It was just Dean and him that night at a random dorm room drinking whatever wine coolers the girls of the dorm had bought. There were quite a few people there and Castiel was chatting with a few girls over by the door. He had no clue where Dean was but figured he was off schmoozing some lady for the night when two of the biggest assholes came marching into the party. They were already drunk and started spurting obscenities at the girls in the room. 

Cas had never been a confrontational person but the one thing Gabriel instilled in him was that you never turn a blind eye to a woman being treated poorly. Without hesitation, Castiel stepped in between the two men and asked them to leave. Words like ‘ugly’ and ‘fag’ were drunkenly slurred but Castiel wasn’t deterred from trying to push the men out towards the hallway. That’s when he felt the first blow to his cheekbone. The second came to his stomach. 

Before he really knew what was happening there were girls screaming and furniture crashing. Castiel had just enough sense to pull himself upright to step out of the way of the flying fists. That’s when he noticed Dean punching one of the men square in the jaw. Castiel heard his friend nearly growling that he’d break the other man’s nose if he ever showed his face again. That’s when the asshole’s friend tried to pick a fight with Cas again, shoving him up against the wall by the throat. Dean was on him in two second flat. Some other guys at the party had finally gotten enough sense into them to help Dean drag the two assholes out of the dorm room. When Dean marched back into the room he pulled Cas out and back upstairs, sitting him on the edge of his bed as he took a washcloth to the cut on his face before forcefully pressing an ice pack to Cas’s forming bruise and nearly threatening him if he took it off. 

It was knowing that Dean would do anything for him that had Cas gearing up to explain what he needed Dean’s help with. 

“With what happened, it left me thinking.” 

“About what?” 

“Is it true?” He asked. 

“Is what true?” 

How was Cas going to explain this next part? He… he needed answers and he definitely needed help. He knew that he could trust Dean to be open-minded and honest with him. It still made him nervous to explain all the thoughts racing through his mind. 

“I’ve never seen sexual purity to be of import. I know some religions or cultures believe it to be valuable, but to me the fact that I’ve not yet had sexual relations is more a reflection of my lack of exposure to others than my lack of desire to engage. But outside of religion and those cultures, is virginity looked at as something of a burden? Would others prefer their partner to be more experienced than not? I still was under the assumption that people enjoyed those who were considered ‘pure’?” 

For a moment Dean looked at Castiel like he’d grown two heads. Clearly that wasn’t where he thought Cas was taking this conversation. “Oh… wow, uh? I don’t know?” 

Castiel rolled his eyes at the non-answer. “You’re sexually active though—what are your thoughts on your partners having had other relations prior to yours?” 

They didn’t really talk about sex. Actually, they almost never talked about it. For all the boisterousness and confidence Dean exhumed, he was still a gentleman when it came to his sexual experiences. Even when Castiel knew Dean was only seeking a woman for one night he never boasted about it, he never made the women he hooked up with seem like a conquest. 

It took a while for Dean to gather his thoughts. 

“Well, I guess I could see his point. Like if you’re looking for a night of fun and worry-free sex you don’t really want to do it with a virgin, because you don’t know how important their purity is to them, even if they say they don’t care but I think everyone’s opinion on it is different.” Cas nodded along as Dean spoke, absorbing every word. 

“For me, too much experience is a little questionable, you know?” Dean continued, “I don’t want to be with a girl who sleeps with a new guy every night, not because I think she’s wrong to do that, but because you can’t be certain that she’s clean—and a one night hook up isn’t going to go get a test for you to be sure. But if I really like a chick, I’m not going to be driven away if they don’t have much experience and I want to see if our relationship could go somewhere.” 

It made sense but left Cas with one burning question, “Do you prefer more experience in a partner?” 

“I mean—yeah, it makes the sex more fun.” 

Castiel nodded thoughtfully. “I think I understand now.” 

He knew what he needed to do. There was no question that if he could gain more experience then he’d never have to go through something like last night again. The only problem was finding someone to help him gain the experience. There had to be someone trustworthy enough. 

“So you’re cool now?” Dean asked. 

“Not quite.” 

“Uhm, okay?” The poor guy looked so confused. Why was Castiel making this so difficult? All he needed to do was ask Dean for help in finding someone. 

“Dean….” 

“What?” 

“We’re friends right?” 

“Yeah, dude, of course we are.” 

“You’d consider us close too?” 

“You’re joking right?” 

Oh god his heart was going to fall out of his chest. Would Dean think this was the most ridiculous idea he’d ever heard? 

“You know I wouldn’t ask something of you if I hadn’t thought about it before hand, right? That I wouldn’t willingly jeopardize our friendship?” 

“Cas? What are you talking about?” 

The more the words started coming out of his mouth the more Castiel realized he wasn’t entirely sure he liked his original plan. Yeah at first he didn’t see a problem with asking Dean to find him another person to help him with all things sexual but now… now he was starting to feel something akin to dread at all the people Dean might suggest. He’d probably suggest someone like Balthazar or maybe even just any stranger at a club and that wasn’t what Cas wanted. 

The wheels in Cas’s mind started churning. What exactly did he want to ask Dean? 

Maybe he’d already known all along. 

He didn’t stop himself as his mouth seemed to speak for him. “This… this might be unusual, but I want you to keep an open mind, okay?”

“Okay?”

“I want to gain more experience… sexually. I don’t want to fall into another situation like the one with Arthur.” 

The face Dean made was a mixture of amusement and shock. “Dude, are you asking me to be your wingman? Because I’m totally up for that.” 

_I should. It’s what I should be asking you because that was my original plan,_ some part of Castiel thought. But that’s not at all what came out of his mouth. 

“No… that’s not what I’m asking.” 

“Really? Then what?” 

Dear lord, he was probably going to throw up. This was a horrible idea. 

“Dean, would you be willing to help me out?” 

“I just said I would.” 

“No… I’m sorry. I’m not making myself clear.” His voice was trembling as he tried to explain exactly what he hoped the other boy would be able to help him with. 

“I don’t want to go through something like last night again. It was humiliating to be rejected like that and I never want to deal with it again. What I want is to have more sexual experience before I attempt to go out and meet other people. I want to know how to be confident and comfortable in the bedroom so that I don’t embarrass myself again. But I know the only way to gain experience is to learn with someone… and I thought… I thought that I could learn with someone I was comfortable with and whom I trusted.” 

“What are you saying?” Dean’s voice was unusually devoid of emotion. 

What was Castiel even doing? His intention was to get Dean to help him find someone, to sift through their friends until they found one that would be willing to help Castiel become a good lover. Why were the words coming out of his mouth the exact opposite of what he’d been planning to say? 

He knew why. 

He knew there wasn’t anyone he trusted more explicitly than Dean. 

He had to at least try. 

“Would you be willing to teach me how to perform sexual favors?” 

Castiel watched as Dean swallowed hard. “Sexual favors?” 

“Yes. Hand jobs and blow jobs seem the first logical task to learn.” 

Dean was gaping like a fish. “What?” 

What was he doing? 

Did he not learn from last night to not put his foot in his mouth? 

But Dean hadn’t punched him in the face or kicked him out… 

Maybe if he just…. 

“Dean, I’d like to learn how to pleasure another person, and you’re the only person I’m comfortable asking for help with. Would I be able to practice on you until I’m ready to try with other partners?” 

“You wanna have sex with me?” 

“I’m not asking for intercourse at the moment. I’d just like to learn how to perform oral sex for right now.” 

“You wanna blow me?” 

Castiel flushed red hot because, lord, if that right there wasn’t a loaded question. But if he wanted to learn how to be a confident lover the first step had to be being brave right now with his answer. Right?

“Yes.” 

“Cas…” 

All this time he hadn’t been able to look Dean directly in the eye but now that he did, he saw a small amount of fear reflected back at him. His heart nearly plummeted into his stomach. Had he just ruined three years of friendship for this? 

Not once did he think this would ruin their friendship. 

But now? 

Fuck, now it looked like Dean was searching for any and all excuses to book it out of the room. 

Castiel could feel emotion starting to prickle at his eyes. 

He was such an idiot. 

“Dean, look. I understand this is an unusual request and that normal friendships don’t have one friend offering to perform sexual acts for the other. I’m also fully aware that you exclusively sleep with woman and that me being a man may deter you from this. I just… I don’t want you to make a decision right now, Okay?” 

Dean didn’t so much as blink. Fuck, Cas might actually cry. He just had to say his peace. 

“All I’m asking is that you take it into consideration. If you decide you’re willing to help me, I promise _no one_ will know. I would _never_ betray your trust and tell another person about it. I also don’t expect anything of you, this would all be me learning how to give others pleasure so you wouldn’t be required to touch me, or even look at me if you didn’t desire… I just ask that you’d be willing to verbally guide me through it all.” 

Castiel waited for a beat, waiting to see if Dean would even nod at him but nothing came. He stood up and moved from the makeshift ‘living room’ and started packing a bag. Even five minutes later Dean still hadn’t moved an inch. Castiel stood near their doorway, fighting back the first sob he knew was coming in order to say goodbye. 

“I know I’ve officially made you uncomfortable so I’m going to leave you for the rest of the night. I’ll stay with Hannah until tomorrow.” 

Again Dean said nothing so Castiel just let the door click shut behind him. 

This rejection hurt worse than Arthur’s.

**Notes for the Chapter:**

> Hmm, I wonder what Dean's response will be. ;)


	2. September 18, 2017

He felt like an asshole. 

Something ugly churned inside of him every time he pictured the look of utter rejection on his best friend’s face. 

Why hadn’t he just said something? Anything! 

But really, what could he say? 

There wasn’t exactly a guide book for what you’re supposed to do when your best friend practically tells you they want to blow you for science. 

It was weird, all right?

But what was weirder was that the more Dean thought about it, the less weird it had become in his mind. 

Yeah, the fact that his best friend wanted to learn how to give good head and had asked him to help was a little weird… but he could see Cas’s logic in it. They were best friends. He trusted Cas with his life and was fairly certain Cas felt the same way in return. It seemed logical enough to want to try and ease your way into the finer parts of sexy times when you had someone you were comfortable with to guide you through. It probably wasn’t the best idea to hook up with a friend though… a significant other would be easier to ease into it all with. But it still didn’t diminish Cas’s logic. 

At the time Cas had asked, it’d just been too overwhelming. Dean had no clue what he was supposed to do or say while listening to his best friend practically promise him unlimited blowjobs. He’d been in shock. But now he was left feeling like an asshole because there was no way he didn’t hurt Cas from his stone-faced look. 

Still he’d needed to sleep on it. 

In his defense, he did extend some sort of olive branch Monday morning when he texted Cas to come home that night. The gesture made him nervous as all hell but he couldn’t let Cas stew in his own worries for another night. 

It crushed him a little seeing Cas’s sad response that he’d understand if Dean didn’t actually want him to come back and could stay away a little longer. But Dean wasn’t going to let that happen. 

Did Cas really think Dean would throw away their friendship over something like this? 

No, he and Cas were solid. Cas had even been one of the first people in Dean’s life he ever felt comfortable dishing out the details of his past. Not once did Cas judge him or show any form of pity for the shit Dean had gone through, he just accepted the facts and went on with life. It was the first time Dean realized that the dorky guy with the perpetually messy hair was without a doubt his best friend. They’d been through a lot together since. So, no, something like this wasn’t going to ruin their friendship. Dean would make sure of it. It might be a little awkward for a few days after they had this talk but they’d be okay. 

Dean knew what he had to do when Castiel came home. He had to tell Cas that it wouldn’t work out. They were too good of friends, and Cas deserved to find someone he cared about to experience all those things with. 

He knew his best friend’s counterarguments would probably be solid but Dean needed to stand his ground. If he did say yes, their friendship would be undeniably altered. Maybe they could work with it and still keep their friendship the way it always had been just with a few side moments for ‘experimenting’ but Dean wasn’t an idiot. Friends don’t remain friends when one of them has had the other’s dick in their mouth. 

He had to say no to Cas’s idea. He’d just be the best damn wingman Cas could ask for instead. 

_Wingman._

He cringed a little. He didn’t exactly _love_ the idea of being Cas’s wingman in order for his best friend to find someone else he could experiment with. What if Dean wasn’t a perfect judge of character and found someone like Arthur for Cas to hook up with? He’d never forgive himself. He cared about the guy, and despite hearing how Cas seemed so indifferent to having sex for the first time he didn’t want Cas to just try out this new sexual side of himself with just anyone. He wanted Cas to have the right person. 

There was really no one off the top of his head that Dean would trust to guide Castiel through his sexual experimentations; no one he could think of would be able to withhold judgment for Cas’s inexperience and over eagerness to learn. And in the end, really there was not one single person he could think of who would truly respect Cas after it were all over. 

No one besides himself. 

Fuck. 

Maybe he was torn. 

Perhaps there was some small part of him who wanted to be able to show his best friend how to be a more confident lover. It wasn’t merely anything more than him being protective of Cas and not wanting him to get hurt… paired with the fact that Dean knew he was pretty good in bed himself. He did have some knowledge he could pass to his friend and they _did_ know each other well... 

No. 

No. It couldn’t work. That Arthur dude had a point… sometimes feelings happen with virgins (or sex in general) and that’s not what Cas needed to happen with Dean. 

It almost frightened him how little the fact that Castiel being a male wasn’t actually frightening him. Not once had Dean ever been with another man. He identified as a straight man but he wasn’t exactly unattracted to men. He had no qualms with silently checking out another man at a club or even on TV or the Internet. It was hard not to, especially when it came to porn. He could definitely appreciate some muscles and a nice cock here and there but he was most definitely attracted to women. 

But the idea of a man… of his best friend, Castiel, giving him head? 

It was an intriguing idea. 

No! 

It was a bad idea. 

Maybe a potentially pleasurable one… but definitely a bad idea. 

God damnit, he needed to stop thinking about getting sucked. 

But fuck that sounded really nice about now. 

Not from Castiel though. 

No. 

No. That’d be weird. 

From a chick. 

Like Lisa. 

She gave good head. 

Well average head. Nothing really could top Rhonda Hurley but that’s probably what happens when you’re nineteen getting sucked off by a twenty-five-year-old. Sets the bar pretty damn high. (It probably wasn’t even that good but he’d gotten maybe a handful of half-hearted blowies before that so everything in comparison was garbage compared to her experienced mouth). 

Fuck. Now he was getting hard. 

Sitting on the small futon they had in the living room section of their dorm, Dean looked at the clock on his phone and took note that Cas’s class wouldn’t be out for another hour and a half, which meant he had more than enough time for some alone time. It was rare that he had the dorm to himself and each time he did he knew he had to use the time to the best of his ability. 

And now with the memories of his dick springing up through the waistband of the silky panties Rhonda had talked him into, as she mouthed at him through the fabric. 

Fuck. 

He needed to get off now. 

He pulled his laptop over from the ottoman and quickly typed in the name of his favorite porn sight. Dean wasn’t too picky with his preferences on what he watched, he didn’t care about what ethnicity the woman he watched were, or if it was just two girls, a girl and a dude, or two dudes and a chick. As long as the video quality wasn’t terrible and the ‘acting’ wasn’t cringe-worthy he always found himself able to get off. 

Right now, he didn’t have anything particular in mind so long as there was a cock getting sucked. He scrolled through the top watched of the week and found one that drew his attention enough. It was of a brunette, on her knees and the time in the corner looked like it was long enough to work him up to completion. 

Shit. This was going to be embarrassingly quick. 

Out of habit, he put his headphones into the port on his laptop, never feeling comfortable listening to the sounds of others having sex through his computer speakers even if he was alone. Dean propped the laptop up on a couple pillows that Cas had bought for the place, and slid down his basketball shorts and boxers, getting into a more comfortable position before pressing play. 

He’d never actually been ass naked on the couch before… always wanting to respect Cas’s space too…. _but_ desperate times. 

Not big on drawing things out when alone, he let out a pleased sound when his hand wrapped around the base of his still hardening dick. For a moment he found himself wondering how long it had actually been since he’d fucked his fist. Fuck, how long had it been since he’d had sex? Like three or four months? What the fuck has he been doing? 

He was pent up and desperate. With eyes on the screen he worked on massaging himself for a while, watching the woman in the video. She was definitely an eager cocksucker, sloppily bobbing her head onto the man’s dick and fisting her hand around the base. The no-faced man had a hand wrapped in her hair, pumping into her face at a steady pace, moaning and grunting with every thrust. 

Shit. He needed that right now. He needed the feeling of a wet mouth to pump into. Spit dripping down his length. The wet sounds of his cock hitting the back of their throat. The sight of full lips stretched wide around him. 

Not having any lube or lotion around Dean pulled his hand away from his dick to spit onto a few times before turning his attention back to his aching member. 

The sloppy editing of the video now had the man in the video licking the woman’s wet hole as he thrust one finger into her, hardly going in past the second knuckle. Even the woman’s sounds were pathetic. Slowly Dean felt his interest drifting away from the events in the video, focusing enough on the woman’s bouncing boobs to hopefully get himself off quickly. 

Drifting his eyes away from the screen because let’s be real nothing is worse than watching people have unenthusiastic, bad sex, Dean nearly had a heart attack. It was then that he noticed a figure drop down in front of him. 

Launching into fight or flight, Dean ripped his hand from his dick and slammed the laptop closed before he realized he’d left himself completely exposed. He tried to haphazardly cover himself with his hands but it wasn’t like he could do much with himself at full mast. 

How the fuck did he not hear Cas come in? 

Fuck! The fucking headphones. 

He pulled them out with one hand and just stared at Castiel, mouth agape. His heart was pounding from the shock. Every ounce of him wanted to scream ‘what the fuck’ but there was something in Cas’s body language that stopped him. 

Cas was on his knees on the floor in front of the futon, staring down at Dean as his chest heaved heavy sighs. Cas’s hands hovered just above Dean’s thighs like he’d only just aborted the movement to actually touch Dean. His pupils were blown and his lips were parted and he was looking at Dean like he was a fucking Thanksgiving feast. 

At the same time Dean dumbly said, “Cas—“ his best friend asked, “Dean… let me?” 

“What?” 

Dean watched as Castiel fought the urge to touch him. He watched as his best friend’s hand twitched in mind air so close to its desired destination. Cas’s eyes didn’t wander though, his eyes stayed locked on Dean’s the whole time. 

“I want to. Please, let me.” 

Dean didn’t know what to say. He was in the in between state of deflating because of the fact that his very male roommate had just caught him jacking off, but the way Cas was staring at him was somehow keeping his dick in the game. His stomach muscles trembled as his body fought to be touched… to have hands on him. Castiel seemed to be able to read his mind or at least his body. 

“I’m not touching you until you say yes. I’m not going to do anything you don’t explicitly consent to. You say no and I’ll never ask again. But I want this. I trust you.” 

Dean didn’t know what possessed him to say yes. But the moment the word left his lips, he didn’t care, as a large hand wrapped around him and stroked him back to full hardness. Dean’s head flew back, hitting the back of the couch with a sigh. 

Holy fuck. 

His body didn’t seem to care that the hand around him did not belong to a woman—no, it only seemed to care that he was being touched. He canted his hips up ever so slightly in approval, feeling as Cas gripped him a little more confidently though lacking finesse. Mini Dean seemed to enjoy the company of another hand because sooner than ever, Dean felt his muscles begin to tingle and tighten all the way down to his toes… it just wasn’t quite enough to push him over. Not yet.

Needing more, he blindly reached to wrap his hand around Cas’s, guiding his roommate’s motions, showing him the twists and the pulls that would finish Dean the quickest. 

“Oh. Fuck!” He grunted, only mere seconds before catapulting over the edge. 

And then he was silently screaming with his mouth open, feeling the ropes of cum spurting out from him, covering both of their hands. His toes fucking cramped with how hard they curled… 

“Oh god.” 

He kept their hands moving for a moment later, wringing out the last of the spasms before he couldn’t take the touch anymore. He dropped his hand by his side as his head lulled against the back of the couch, trying to catch his breath. 

One… two… three breaths and the reality of what just happened hit him square in the gut. 

What had he just done? 

He refused to open his eyes. He couldn’t look at Castiel right now. He couldn’t…. what the fuck did he do? 

This was exactly what he wasn’t supposed to do. 

He waited for Cas to say something but nothing ever came. Eventually he heard the sink from their on-suite bathroom turn on. 

Dean only opened his eyes when he felt his groin being tenderly wiped down like it was a completely normal thing for his friend to just be wiping down his dick. 

“I can—“ 

“It’s okay.” Castiel didn’t take much longer in finishing. After he wiped the last of Dean’s come away, he leaned down just enough to start tugging Dean’s shorts back up. There was something so weird about feeling his best friend tuck his flaccid dick back into his shorts that Dean couldn’t even find words to protest. 

Then there was silence. Neither he nor Cas knew what to say to one another. 

Castiel was now sitting on their ottoman across from Dean, steadfastly keeping their limbs from touching. 

Dean could feel his heartbeat pounding in his ears. There was no way even Castiel and his frequent lack of social cues couldn’t pick up on the awkward tension growing thick within the room. What could Dean even say? Except to apologize a hundred times over for allowing something like this to happen… fuck. He couldn’t believe he’d let himself say yes. 

What the fuck was he thinking? 

“You’re uncomfortable.” Cas finally said into the void between them. 

Dean’s first instinct was to say ‘duh’ but he knew he’d be lying. Or half-lying. He was only uncomfortable with the fact that he’d put Cas into this situation not the fact that his best friend had just jerked him off. 

“I’m not uncomfortable.” 

Castiel didn’t seem to hear Dean because his rambles overlapped. “I know I just overstepped. I shouldn’t have done that. I’m so sorry if you feel like I took advantage of you. I’m so sorry Dean. I’ll understand if you can’t forgive me.” 

The genuine worry in Cas’s voice gripped at something in his chest. “What? You think you took advantage of me?” 

“You didn’t want that. I shouldn’t have pressured you.” 

He had to stare at the blue-eyed boy across from him for a moment to let what Cas said sink in. Cas’s eyes were wide with worry in a way Dean hadn’t seen since the other boy thought he’d failed his first final freshman year. Of course, they were both worrying about the same thing right now. Dean thinking he’d just used Cas for his own pleasure and Cas thinking he’d just taken something from Dean that wasn’t given explicitly. 

Dean hated that look, and he was determined to make sure to fix it right away. “I didn’t want that? Cas I knew what I was saying yes to and if you missed it, I kind of just came harder than I have in a really fucking long time. I wasn’t pressured into anything. I’m not upset with you. I’m upset with me. I shouldn’t have said yes because what the hell does this mean now? This changes things.” 

He should have thought that last part over before speaking because now Cas’s eyes were wild with fear. 

“How?” 

“You’ve had my dick in your hand. That’s not exactly what friends do!” 

“But it’s what I want us to do.” Cas rushed to say, looking desperate for Dean to understand. “There is no one I trust more than you and I know this could work. I just want to be experienced… even just now you had to assist me because I wasn’t doing it right and I want to learn, Dean. I want to learn how to bring you or another man to orgasm without assistance. I want to be good at this.” 

Dean could feel his resolve slipping between his fingers. He knew somewhere deep down that this was probably the worst idea but… they’d already done this one thing. What could a few more tries change? If Cas wanted to learn he wouldn’t mind helping but… that didn’t mean he wasn’t going to at least try and show reason to his best friend. The guy had to understand that there were other ways to go about this. This wasn’t Cas’s only option. 

“It just takes time, Cas. It takes a lot of awkward fumbling and weirdness before you get it right.” 

“But I don’t want to deal with that!” Cas groaned petulantly. “I want to get through all the awkward parts with someone now. I want you to help me. Will you please help me?” 

He let the silence grow between them as he contemplated his answer. He knew their friendship was strong enough that if he took the sensible approach and turned Cas down, they’d be okay. Of course, they’d both know that something had happened between them but they’d figure it out. He just…. He couldn’t get the idea out of his head that if he told Cas no that his best friend would try and find someone far less suitable to help him than Dean. He was terrified that the other guy would end up hurt in a way that Dean could have prevented if he just helped him. 

And that fear, the fear of doing wrong by Castiel had him asking…

“How would this even work?” 

Even Cas seemed stunned by Dean’s seeming acceptance of the arrangement. 

“Really? You’ll do it?” 

He felt like there was a lump in his throat but he swallowed around it. “I’m considering it. Just walk me through it.” 

“Well… I hadn’t really… I’m not really sure…” Castiel floundered for words like he hadn’t once expected to hear a yes from Dean. Dean still wasn’t convinced this was a good idea but if he was going to do this he needed to know all the details. 

“How would the uh… learning… happen? Or start?” 

He felt stupid not being able to say ‘Hey Cas, how will I know when you want to blow me?’ but Cas didn’t seem pulsed by his word choice. 

“Uh… well, how about when either one of us feel like… _learning,_ we can ask the other person? If we’re both in agreement we… we uh… practice. But if one of us isn’t feeling up to it, we drop it? We just have to communicate.” 

Dean nodded along dumbly to what Cas was saying. It sounded reasonable. He just needed to know more… “What all do you want to learn?” 

He could see the possibilities roll through Cas’s mind and Dean had to admit that it made him very nervous. He wasn’t sure how far he’d be willing to go for this. He’d never entertained the idea of doing anything sexual with a dude but hand jobs and blowjobs seemed innocent enough. Dudes in college experimented with those things sometimes, right? Just to see if they even liked it? 

But would he be okay with doing more? He didn’t think he could like… return the favor or something. He didn’t think that’d be something he’d want to do… toeing a little too close to _something_ he wasn’t quite certain on. But maybe that wasn’t on Cas’s radar currently? 

Castiel must have picked up on his hesitance because he looked Dean sternly in the eyes. “Anything that you’re willing to teach me. So long as you’re comfortable with it.” 

Oh shit. He was really doing this. 

“Should we have rules?” 

Tension seemed to finally drain out of Cas’s shoulders and it took a moment for Dean to understand how much this actually seemed to mean to Cas. Dean had been so blindsided by the idea that he didn’t take a real moment to think of this from Cas’s point of view. Dean had been fifteen when he’d lost his virginity to Cassie Robinson, equally a nervous virgin on their sophomore Homecoming night. He never really thought of what it would feel like to try and put yourself out there at twenty-one, only to be turned down for not having experience. But Cas’s pure relief at Dean’s acceptance of the arrangement had him realizing for the first time just how vulnerable Cas had probably felt. How the rejection the other night had made him try and seek out a solution to the problem. 

Some part of him was terrified he’d fucked everything up between them by saying yes, but on the other hand, seeing Cas perk up like he’d been given a gift made Dean bite his tongue. 

“Of course, we can establish rules, if that makes you more comfortable.” 

Dean put on his best winning smile. “It’s probably best. Where do you think we should start?” 

“How about basic ones for now and we can come up with others as we go?” 

“What do you have in mind?” 

“I think…” Cas trailed off, contemplating. “I think it would be best if we don’t tell anyone about this for starters. I don’t want anyone assuming things they have no clue about.” 

Dean tried not to make his sigh of relief obvious. He didn’t think he could handle anyone around them finding out that they were “learning” things together in their spare time. “I think that would be best too.” 

“And… I feel we need to check in with each other regularly to decide where our comfort levels are. If either one of us wants to stop this at any time we stop, no questions asked.” 

“That’s good.” He was thankful Cas seemed very keen to keep Dean comfortable and not ask for more than he was willing to give. 

Cas fiddled with his pant leg as he worked up the courage to reveal his next rule. “And… no sleeping with anyone else?” 

“That’s fair.” Dean responded without hesitation, making Cas’s head whip up. 

“Really?” 

Dean had to fight the instinct to take the shock in Cas’s voice personally. Of course, he wouldn’t go around sleeping with other people if he and Cas had this arrangement going on. He might not be a saint but he’d never been one to sleep with multiple people at a time. Plus, he’d never put Cas at any sort of risk of contracting something, no matter how much protection Dean always used with other partners. 

“Really. Until we decide you’ve learned enough. It’s not a big deal to me.” 

Cas’s smile was genuinely grateful. “Thank you.” 

“So we’re doing this?” Dean asked through a nervous smile of his own. 

“As long as you’re sure.” 

He knew he wasn’t sure if this was the _right_ choice but in making this choice he was sure of two things. 

1\. Castiel Milton was his best friend and he’d do anything for him. 

2\. He didn’t want anyone else helping Cas with this. 

“Free blow jobs whenever I want? I’m sure.”

**Notes for the Chapter:**

> *is nervous*   
I hope you all like where this story will go. This is just the start :)


	3. September 21, 2017

From the moment their agreement was sealed everything seemed to snap back to normal.

Even after their talk and Dean explicitly agreeing to helping him out, Cas had been doubtful. He knew Dean better than he knew anyone and that meant he felt pretty confident in predicting his friend’s reactions but Dean just wasn’t reacting the way Cas had anticipated. He’d expected anxiety to roll off his friend in waves and for Dean to clam up in his worries and stop talking to Cas because he’d realized that he regretted letting Cas give him the hand job. 

None of that was happening though and Cas didn’t know what to think. 

He wasn’t going to ruin the normalcy by mentioning anything. Instead, he was going to roll with it and allow himself to be excited that Dean had agreed to help him. They had rules and mutual understanding between them and Cas was filled with nervous excitement. 

He had to resist asking Dean if they could start ‘learning’ (as they’d been calling it), that very night, thinking it might be too soon to bring it up but it was definitely, _definitely_ on his mind. Instead, he just took Dean’s cues, and readily accepted when his friend asked if they could just play some video games together and order pizza. It was all so normal. 

Now, knowing that he could think about it, the possibilities of what he could learn were on Cas’s mind all day every day. It’d been a few days since Dean had agreed to help him but for some reason every time he thought about asking Dean if they could proceed with their arrangement his nerves got the best of him. He knew he was going to be bad at it but he didn’t want to be so bad that Dean would think of this as a chore. But Dean had promised to teach him, right? Logically, if Castiel were bad at it, he had to at least trust that Dean would guide him into doing things the correct way. Right? 

The normalcy lasted only a few more days before Cas couldn’t fight off the anticipation anymore. He figured a Thursday night would be best anyway since they didn’t have classes on Friday and it’d give them the whole night. Not that he thought it’d take the whole night… but if it did, they at least had more time… Yes, he was quite nervous. 

He didn’t think this part through when he’d first thought of doing this with Dean. He hadn’t looked past actually having Dean agree so now, thinking about how to even approach the subject again made him feel like his heart was going to beat out of his chest. He _knew_ that Dean had already agreed but per their rules, either of them could say no to doing something if they weren’t up for it… what if Dean said no? 

His mind was a flurry of ‘what if’ scenarios as they watched a movie together, Dean on the navy-blue futon, and Cas on the fast food stained brown beanbag. He didn’t think Dean could tell that he kept glancing over every few minutes trying to gauge Dean’s state of mind. 

Would he be interested? 

Was he in the right mood? 

Should Cas leave so that Dean could watch some porn or something to get in the right mood? 

Should he just wait until tomorrow night? 

The questions were gnawing at Cas to the point he thought he was going to explode. He just needed to be brave. Dean had agreed to this, hadn’t he? 

All Cas had to do was ask. 

Before he could second-guess himself any more, he felt his vocal cords release a hoarse, “Dean?” 

His friend didn’t bother looking away from the screen. “Yeah?” 

“Can we uh—” Cas’s voice shook with each syllable, causing Dean to turn away from the movie to catch his eye. “Can we… you know?” 

There was an audible gulp as Dean straightened up in his seat. He seemed unsure of his own voice too. “You want to?”

Cas felt himself faintly nodding. “I want to learn.” 

It seemed to take a minute for Dean to wrap his mind around what Cas was asking but before Cas could stress too much about rejection, Dean was nodding in return. “Oh—okay. Okay, yeah.” 

“Do you want… do you want the same as before?” 

“The same? You mean….” Dean watched him as Castiel pulled himself from his spot on the beanbag and moved to sit in front of Dean on the ottoman. His roommate seemed almost as nervous as Castiel felt. “Like… the last time we…. Uh, uh yeah? Or whatever you want to do…” 

Cas bit his lip and slid off the table to kneel in front of Dean. Butterflies were on a rampage in his gut. He fought through it though, willing himself to just ask for what he wanted. “I think… I think I’d like to uh—I think I’d like to use my mouth too.” 

Dean’s mouth dropped open for a split second like he was going to say something. He shook his head before saying, “Right. Right, yeah. Yeah, that’s fine.” 

Last time it’d been… easier, per say. Last time Cas had walked in and seen his best friend bare from the waist down and had just kind of—reacted. Dean had already been aroused, had already been close to orgasm and so it wasn’t exactly all Castiel’s doing that his friend had gotten off. But now… now he needed to get them from point A to point Z and he didn’t know where to begin. 

He tried not to let himself feel like an idiot. 

“What should I do?” 

He wasn’t sure if Dean didn’t understand the question or if he was as nervous as Cas because it took the other man a while to answer. 

“Oh, I’ll just uh—I’ll just take my pants off I gue—“ 

“May I?” Cas cut in rather abruptly. 

“Hm?” 

“May I undress you?” 

Cas had never seen Dean’s eyes quite so alert, perhaps alarmed, but still his friend was nodding in agreement. 

“Yeah, okay. Okay, yeah.” 

Cas dropped to his heels, and nudged Dean’s knees apart, but was careful not to invade too much of the other man’s space—as ironic as that seemed. His hands were a little shaky as he tentatively reached forward going straight for the ties of Dean’s sweats. 

“Wait.” 

Cas’s hands flew back to his side like he’d been shocked. “I’m sorry.” 

He couldn’t look up. He’d completely understand if Dean had changed his mind but Cas kept his eyes turned down towards the carpet under Dean’s feet not wanting to see the look of rejection on his friend’s face. 

But Dean dissuaded his fears immediately. “No… No. Don’t be sorry! I just—I just…. You want to learn and I’m not doing much teaching.”

“What do you mean?” 

Castiel noticed that Dean was fumbling with his words as much as he was, which helped to calm him down moderately. “You don’t have to do this, but uh—when you… when you want to make your partner like, really excited, you gotta… you gotta drag it out.” 

“What do you mean?” 

“Unless you’re both like desperate to get to the good stuff, a lot of the time the best part is the buildup.” 

“Okay.” Cas stated, soaking up the advice even though he couldn’t say he fully understood how prolonging the ‘build up’ could be considered the best part. Wasn’t the best part climax? He listened to Dean’s advice nonetheless. 

“It’s all about getting things heated. Just now we were watching Hunger Games and like—that isn’t the most sexy setup.” 

“Oh—I’m sorry.” 

“No, no, no!” Dean stopped Cas’s negative train of thought before it started. The green-eyed man seemed almost confident now. “I’m not trying to make you feel sorry, just, if the goal is to go from 0 to 60, you can start ripping clothes off and just get on with it. _But_ if you want it to be more memorable and seductive, you gotta ease into that.” 

“How… how would I do that?” 

“Uhm, touch. Touch is a good thing. Like slow hands and stuff… Playing with the button or zipper or whatever to tease them a little bit…. You know, stuff like that.”

Cas was still shaking a little nervously as he leaned off his heels. This was the type of direction he needed to hear to know where to begin. Slowly, he placed his hands on Dean’s knees and almost feather-light, slid them up his thighs stopping well before he got anywhere near the waist band of Dean’s sweats. 

“Like this?” 

“Yeah, that’s a good start.” Dean encouraged. He’d shifted down the seat a little more to spread his legs wider, letting Cas between them more easily. “But I feel like I have to tell you again that you _don’t_ have to do what I’m saying right now, it’s all just for future reference.” 

“I might as well practice.” 

“Yeah, yeah, okay,” Dean agreed quietly. 

Cas looked down at the man in front of him. Of course, he knew Dean Winchester was attractive but even in his holey, grey sweatpants and a stained ACDC shirt, he still managed to look incredible. It was no doubt the sharp lines of his jaw, peppered with light scruff, paired with the natural muscular build that filled out his shirt, and those bright green eyes that currently shone with nervous but undeniable trust… that all had Cas feeling braver suddenly. 

“Should I keep going?” 

“Yeah. Just do what you think feels natural I guess? I’ll tell you if it’s weird.” 

Cas took that as a sign to get things moving along. He restarted the movement of his hands, now trailing up Dean’s thighs heading towards the waistband again. Right before he made contact, he hesitated. He didn’t know where he should go from there. To continue running his hands over the muscles hidden beneath Dean’s clothes or jump to the removal of said clothes? 

Just when Dean was about to say something, Cas’s mind was made up. 

His right hand began its ascent, trailing up, up over Dean’s t-shirt clad stomach and over his sternum until it reached his neck and trailed back down. He tried to take Dean’s advice and do what felt natural, so Cas let his left hand trail back down his best friend’s thigh, his thumb moving to brush against the inner part of Dean’s upper leg. Dean’s legs instinctively parted further; encouraging Cas to bring his palm closer to where he hoped Dean was building in his pants. 

“That’s good.” Dean whispered in encouragement. 

“It is?” 

“Yeah. Definitely.” 

Emboldened, Castiel kept with the touches for a while longer before drawing the courage to undo the ties of Dean’s sweat pants. It was then that Dean lifted his hips, allowing Castiel to slip his fingers under the band of Dean’s sweats and boxers and slide them down. 

Warmth filled him as he watched Dean’s hardness spring free and land on his stomach with a soft bounce. Castiel didn’t know how to describe the relief he felt having visual evidence that Dean was at least aroused. Only then had he realized just how nervous he’d been that Dean wouldn’t be able to get it up…

He pushed those thoughts aside as he released each of Dean’s legs from the confines of his clothes before settling more securely into the space between his knees, and gazing down at Dean’s enticing length. Castiel had nothing besides himself to compare it to but he knew that Dean was perhaps average in length, but slightly above average in girth. It was without a doubt a very appealing sight. 

“Maybe don’t stare at it like it’s a science project.” 

Cas’s head whipped up and his cheeks heated profusely. “Sorry, sorry! It’s just last time I didn’t really look at it and I thought that—“ 

“Hey, it’s okay.” Dean said with a shy smirk. “But it makes a guy a little insecure when someone just stares at it…” 

Castiel looked back down, appreciating. “You shouldn’t be insecure, you’re definitely well endowed, larger than myself actually.” 

“Geeze Cas, okay…” He watched as Dean dragged his hand over his face. The tips of his ears were suddenly red. 

Damnit, Cas was already screwing this up!

“I’m making you uncomfortable.” 

“Honestly? Not really. It’s little strange, but all new encounters tend to be at first.” 

The look in his eyes made Cas know he was being honest but Cas didn’t want to ruin the moment by talking anymore and maybe saying the wrong thing. Instead, with more skin to touch, he let his hands roam up and down Dean’s lightly hairy thighs and up over his trembling stomach. Now that he was allowed to touch, he felt like he couldn’t do it enough; he wanted to put his hands on every surface of Dean’s body but that wasn’t what he was here for. 

He attempted ‘teasing’ only for a few moments longer, moving up and down Dean’s torso, grazing his wrist or knuckles over the head of Dean’s dick with each pass (more on accident than anything) but Cas learned that he already loved the small inhales that were crossing Dean’s lips with each pass. 

Needing to know if he could pull any more sounds out of Dean and not having much more patience, Cas finally slid his hand up and over Dean’s hardened cock and gripped him firmly. He stroked him as he had last time before Dean croaked out, “Lick your palm.” 

“What?” Cas asked, pulled from his slight trance of knowing he got to do this to Dean. 

Dean tugged at Cas’s hand, making his words finally register in Cas’s mind. 

“Lick your hand or spit...” 

Castiel did as asked and soon was gifted a total body sigh on Dean’s part when his slicked hand wrapped back around. He moved his hand the way Dean showed him, making sure to twist at the top just the way Dean said he liked best. It wasn’t long before he was able to see the way Dean was reacting to his ministrations—Dean sank lower on the couch with every arch in his back. 

Dean wasn’t touching him, not that Cas was surprised but out of curiosity he looked up to his friend, wanting to know what he looked like. One of Dean’s hands had found its way to his hair, while the other gripped the couch cushion by his head; his eyes were scrunched closed, his mouth open, and he looked completely blissful. Cas looked back down at the cock moving in and out of his closed fist, feeling inequitable want course through him as he noticed the precome dripping from the tip. 

He felt emboldened at the moment and didn’t hesitate to lean his head down just to get a taste of Dean. He licked softly at the head, and heard a resounding moan escape from above him. 

“Was that okay?” Cas asked quickly, needing to know if he’d crossed a line or not.

“Yeah.” Dean said through a breath, before finding his voice. “Yeah… yeah that was good. You can do that again. Only—only if you want to.” 

So Cas did. One, two, three small licks and then he was certain he wanted to take it a step further. Moving his mouth to the base of Dean’s shaft, Castiel flattened his tongue and dragged it all the way to the top savoring the taste of _Dean;_ faintly salty but a twang of soap? He didn’t think past the flavor when he felt Dean suddenly shiver. 

“That’s good. Yeah, that’s really good.”

Cas preened under the praise, allowing the words to flood him with bravery. After pumping his wrist in a few more strokes, Castiel finally open his mouth to let Dean in. It was… intimidating to know that he had his lips around Dean’s cock. That he was giving his best friend a blowjob—the first he’d ever given. And… he liked the fact that he was doing it. Dean filled up his mouth far more than he’d anticipated but the weight of him in Cas’s mouth made his own body flood with heat. 

He obviously knew no practical skills in this regard but had watched enough porn to know than licking, sucking, and bobbing were all techniques that seemed to be highly encouraged in giving head. So, Castiel went with his best instinct, licking around the girth in his mouth as he moved his head shallowly up and down—his hand still moving in tandem at the base of Dean’s shaft. 

“Ah! Yeah! Like that…” Dean gasped, his hand now finding the side of Cas’s head, trying to urge Cas off. Cas pulled off for a moment, glancing up at him behind his lashes as Dean panted out more directions. “Don’t try… don’t try and take it all. Just do what you can,” 

With a small nod, Cas went back to it, a shiver running through him as Dean breathed, “Yeah… yeah… that’s good.”

Soon, Dean’s instructions started coming out in staggered breaths, telling Cas when to speed up or slow down. Castiel knew he wasn’t going to be able to take Dean’s length down his throat just yet but he did what Dean told him to do with his hand still working the shaft, to make sure that it was still pleasing. 

His knees were starting to ache from the carpet pushing against them and his jaw was definitely becoming sore from this new use for it but Cas’s own cock was throbbing from a burning desire to touch himself. The sounds and moans Dean was making just from Cas’s hand and mouth were more of a turn on than Castiel ever expected. It maybe should have scared him how much Dean’s arousal affected him, but he didn’t care. He loved that he was able to get this kind of reaction. 

_He_ was the one who was drawing these noises out of Dean. 

Suddenly his hair was being gripped tight and before he could even grunt protest, his mouth popped off Dean’s cock with an obscene smack and Dean’s release was being ejected onto his hand. 

Castiel stared wide-eyed at the blissed-out look on Dean’s face before hoarsely asking, “Was that okay?” 

“Are you serious?” Dean asked with a breathy laugh but Cas wasn’t entirely convinced it was okay. Dean must’ve seen Cas’s trepidation face because soon after he said, “Yeah, Cas, it was better than okay.” 

That felt good to hear, amazing really. He smiled to himself a little, hoping he didn’t look too ridiculous grinning about giving a mediocre blowjob. He was still reeling a little from the fact that he’d gotten to do that when Dean lethargically patted the space on the couch next to him and said, “Come up here, your knees and neck are probably killing you.” 

Cas followed the command, but found himself uncertain of what he should do. Currently Castiel himself was hard in his pajamas, with a some come on his hands, as his best friend sat bare from the waist down calming down from his orgasm. Did he go clean them up? Did he need to help Dean into his clothes again? Should he just go shower and get himself off? 

He didn’t know if he should ask. 

“You need to get off?” Dean broke into his thoughts. He looked over at Cas with a hint of shyness. “You can—uh, you could like lean against me as you do it… or whatever. I don’t mind.” 

“No… no.” Cas insisted, not wanting to impose his own needs on the other man. The deal was that Castiel would learn to pleasure Dean so Dean didn’t own him anything in return and Cas wanted to stick to that. He didn’t want to needlessly make his best friend uncomfortable. “I’ll just go take care of it in the shower.” 

Dean seemed, perhaps, hesitant to let him go. “Okay. If you’re sure.” 

“I am.” Castiel confirmed, before turning a bit more bashful. “Uh… Thank you. For that.” 

“I should be thanking you, dude.” 

“You’re the one teaching me though.” Castiel insisted but Dean didn’t seem impressed. His friend had a look of discontent on his face suddenly, making Cas nervous. 

“You don’t need to thank me, okay? Not for any of this.” 

“Okay.” 

Dean offered him a kind, but sad smile. “Go shower, okay?” 

Following Dean’s orders, Castiel went off into the shower. He took care of his still-proud erection before quickly cleaning himself up and slipping back into his pajamas. He couldn’t quite pinpoint the feelings he had coursing through him. 

He’d actually done it. He’d given his first blowjob and it was successful. He felt good about it afterwards too, a sense of relief even, it was almost some sort of accomplishment knowing that there wasn’t anything so wrong with him that someone wouldn’t enjoy feeling his mouth on them. He knew it was probably nowhere near the top of Dean’s list of preferable blowjobs but his friend had seemed satisfied enough. The look on Dean’s face afterwards was what left Castiel unable to feel completely content with the events of the night. There seemed to be something plaguing Dean’s mind and that unsettled Cas greatly. 

Did Dean not want to go further than just one night? 

By the time he came back into the room, Dean was cleaned up and dressed again. The other man smiled at Cas from across the room. “Wanna finish the movie?” 

“Yeah. Sounds good.” Cas responded, walking across the small space towards his beanbag feeling relived that Dean didn’t look so disturbed anymore. 

Before he could even move to sit, Dean’s hand softly connected with his lower arm, forcing Cas to stop his movements. “Come over here.” Dean commanded gently. 

Cas followed Dean’s wishes but that didn’t stop him from questioning them. “Why?” 

“I’m making a rule.” 

“What rule?” 

There was a hint of trepidation in Dean’s words, but his eyes showed sincerity. “We… we uh…. We cuddle after.” 

“Cuddle?” 

“I’ll shoot you if you ever tell anyone I like to cuddle,” Dean growled jokingly but followed, with another shy smile. “But yes, cuddle. You’re my best friend Cas and even if you don’t see it this way, this is all kind of a big deal. Cuddling after just feels nice.”

“You want to cuddle with me?” Castiel asked dumbfounded but Dean didn’t seem to be uncomfortable with the arrangement, instead it felt like he genuinely was asking for this. 

“After we do anything, yeah. Just for a short while after at least.”

“Okay. We’ll cuddle after.” 

A small bundle of nerves settled inside of him as Castiel moved onto the couch and leaned against Dean’s side. He let Dean take the lead from there, throwing his arm around Cas’s shoulders and pulling him in until Cas’s cheek rested on Dean’s shoulder and his arm settled over Dean’s waist. They both kicked their legs up onto the ottoman and turned their attention to the TV to finish their movie. 

As they laid there for the remainder of the movie, Cas tried not to let his thoughts cloud his mind but there was one thought that he couldn’t exactly wash from his mind with the smell of Dean’s soap infiltrating his senses:

Perhaps he was a little in over his head.


	4. October, 2017

“Castiel?”

Dean could hear his friend, Benny, calling his roommate’s name but Dean refused to turn his head away from the screen where Benny was currently kicking his ass at Call of Duty. He could admit he played the video game a little too much but it was nothing compared to his friend. Benny was far better at this game than should even be possible. 

Cas took a while to answer, which meant the guy was probably still nose deep in his textbook. 

“Yes?” Dean heard his roommate speak. 

“Would you mind looking over my paper when I’m done with it? Dean said he would but you know his brain doesn’t get along with grammar too well.” 

Dean had to laugh at Benny’s lighthearted jab. There was a reason Dean wasn’t becoming an English professor in his future; he wasn’t terrible with words but he definitely wasn’t as good with them as he was with math. That’s why engineering was his career path. “Can’t help it, I’m a numbers guy.” 

“Sure, I can look over it,” Cas agreed kindly. “Is it due soon?” 

“Not until next Friday but I’ll be done with it by tomorrow.” 

“Just email it to me.” 

“I owe you.” Benny groveled and Dean could hear Cas’s laugh in return. 

There were a few more minutes of conversational silence, with only the sounds being Dean cussing at Benny for killing him, yet a-fucking-gain, even though they were on the _same fucking team,_ before Benny started chatting again. 

“So you two have any plans for the 3 day weekend at the end of the month?” 

With one more failed attempt to get revenge on his friend, Dean chucked his controller onto the ottoman, officially throwing in the towel. 

“Not yet,” Dean answered for the both of them, knowing already what the other guy was planning to do for break. “Tickets back home cost too much for that weekend and Cas’s dad is back with his psycho ex so he’s avoiding that shit show.” 

Benny’s eyed both of them with a confused stare. “Psycho ex?” 

“Kali is… an interesting character,” Cas offered diplomatically and Dean could feel himself roll his eyes. His friend had a knack for underplaying other people’s shortcomings. 

“Cas.”

Dean eyed his friend exasperatedly, not allowing him to just leave his description of his dad’s girlfriend at that. He knew Cas wouldn’t mind telling Benny this stuff, or else he wouldn’t have pushed for more details. Dean also knew Benny would get a kick out of some of the stories Cas had up his sleeve about Kali. 

Cas must’ve agreed since he turned towards Benny, abandoning his homework, and looked ready to dish it all out. 

“She has an explosive personality and tends to break things whenever Gabriel does anything against her wishes.” 

“Like leave a dish on the counter…” Dean chimed in, emphasizing just how ridiculous Kali’s tempers were. He could never forget the time Cas face timed him on summer break one time to show Kali throwing Gabriel’s clothing out of the window just because he’d left the toilet seat up and she’d fallen in. 

“She is very much hot headed and likes to know everyone just how displeased she is by throwing things and breaking anything in reach,” Cas agreed, laughing despite himself. “She also doesn’t really like kids so that caused some problems between them.” 

Despite the eyeroll Cas had ended his sentence with, Dean knew deep down it kind of bothered him. It seemed to have perturbed Benny as much as it did Dean the first time he’d heard that too since the other man grimaced and asked, “Why’d your dad stay with her?” 

Cas sighed, “She’s a former porn star and my dad thinks with his downstairs brain about eighty-five percent of the time.” 

He had to chuckle at the monotone way Cas delivered that sentence. He looked over at their friend and waited for Benny to pick his jaw off the ground because, yeah, Benny and Dean were definitely like-minded when it came to these things. Cas’s dad managed to sack a porn star? It wasn’t that Gabriel was bad looking but he was shorter than even Cas and usually dressed pretty goofy but he was funny as hell so Dean wagered that helped a lot. 

“Dean, have you met her?” Benny asked wide-eyed, “Tell me you’ve met her.” 

“Sorry. Can’t say I have.” 

“Damn, wanted to know if she’s hot.” 

“Trust me, I want to know the same thing,” he replied with a mirrored eye-waggle to Benny’s. The two laughed when Cas called them pigs. 

What Dean didn’t mention out loud was that he’d, absolutely, looked her up the same day Cas had told him about the fact that his on and off again ‘step-mother figure’ was a porn star. And Dean had almost gotten his rocks off to one of her videos until it finally dawned on him that Cas’s squirrely looking, hyperactive, always calls him ‘Deanie Weanie’ dad had been with her. Then the video was more revolting than anything. 

“I assure you both that she’s beautiful,” Cas said with a over exaggerated eye roll, “but trust me when I say when you see her throw a frying pan at your dad’s head, the beauty fades a few degrees.” 

“Crazy is always hot. Always.” Dean jokingly affirmed. Just to get Cas to stick his tongue out at him petulantly. Needing to up the ante Dean threw the bird his friend’s way, pairing it with a flashy wink. 

When their little silent banter ended, Cas seemed to have officially given on with whatever he’d been working on and sloppily piled his work onto his desk before moving around their room to shrug on his overcoat and tuck his wallet into his pocket. 

“Where’re you going?” Dean asked, curiously. 

“Dinner with Hannah.” 

There was a dramatic sigh from the big man in the room and Dean glared over towards where Benny was looking at Cas with a dramatic frown. Dean knew instantly what Benny was going to say and by the _‘This again?’_ look on Cas’s face, Dean’s best friend knew it too. 

“Cas… when are you going to let me have her number?” It was almost pitiful the full-fledged whine Benny’s voice undertook every time he talked about trying to get Cas to be his wingman with Hannah. He’d been at it for almost a year but Cas was just as protective over Hannah as any. 

“I think the better question is when are you going to get the nerve to actually ask her out yourself?” 

“You know she’d just laugh in my face,” Benny argued. Dean nearly pulled out his phone to capture a picture of the burly man looking like a sad teddy bear. 

“Maybe if you hadn’t spilled a beer all down your front the first time you tried to talk to her she may think of you in a higher regard,” Cas teased, knowing just how to embarrass the man. 

Benny didn’t seem deterred though. 

“One day I’m gonna win a date with her.” 

Cas patted himself down again, checking he had everything he needed. “I won’t hold my breath,” he jeered, making Benny feign heart problems. 

Right before Cas was leaving, Dean as usual called out, “Hey, which place you guys going?” 

“Burger Time.”

“You have your phone?” 

“Yes.” 

“Okay. Text me when you’re on your way home.” 

“I will.” 

“Be safe. You’re walking Hannah back right?”

“Of course.” 

“Okay cool. Have fun.” 

He didn’t think anything of their conversation until Benny busted out laughing a few moments after Cas shut the door. “You’re such a mom. Do I need to run back out there and make sure he has clean panties too? A snack for the road?” 

“Shut up, asshole.” 

He threw a solid punch into the meat of Benny’s arm for good measure. 

“I get it though,” Benny admitted after landing a solid hit into Dean’s own arm. “Me and Ash ask the same questions. Too many crazy things happening in the world these days.”

Dean shuddered at the thought. There were too many fucked up things happening in the world but a disturbing amount at college campuses as well. He knew for the most part that their campus was safe but one could really never be too careful. Dean said as much. 

“I agree.” Benny replied thoughtfully. At that moment Dean got up to go grab himself another beer, offering one to his friend who kindly turned it down. “So, how’re you doing, brother?” 

Dean slumped back into the couch and shrugged at his friend. “I’m good. Why?” 

“Haven’t seen a lot of you since the semester started.” 

A wave of shame hit Dean a little at the words. He had to admit that he hadn’t been as social the past few months but especially less social in the most recent weeks with the sudden turn of events between him and Cas. He tried to play it cool though and not let on that he was keeping a giant secret. 

“I’ve just been here. Mostly bumming around.” 

“Getting old?” Benny joked. “Too cool to go out now?” 

“Just not really feeling it, you know?” And that was the truth. Ever since coming back from summer break, Dean just hadn’t felt so up for going out and partying anymore. He hadn’t exactly been a big party man before but every few weeks he could be talked into going out with Benny, Ash, or Vic. He’d manage to drink a few, pick up some chicks, and have a good night but little by little it stopped being fun to him. 

He found the time he got to sprawl out on the couch with a pile of junk food and Cas sitting next to him in his vile looking beanbag, was the way he liked to spend his time best. And now? Now with the new arrangement they had going, he couldn’t find any excuse to actually want to go out. 

“Yeah, I get it,” Benny agreed. “The freshman coming in look like they’re fifteen and act like they’re ten. It’s not as fun as it used to be.” 

Dean nodded in solidarity. He realized too that he had been missing his friends. Benny was an awesome dude and a lot of fun to hang out with. It was shame that Dean hadn’t been seeking out his company as much anymore when they were still able to. Adult life was right around the corner, after all. 

Benny must’ve had the same thoughts. “We need to hang more though. If I have to listen to Ezekiel and Gadreel go at it one more time I’m going to lose my mind.” 

“They still fighting?” 

“Then making up. Then fighting. It never ends.” Benny grimaced. Both he and their friend Ash had reluctantly accepted moving into a four-bedroom home with Benny’s older cousin Ezekiel and Ezekiel’s on and off again boyfriend Gadreel. But Benny and Ash justified that the rent was cheap and Zeke always paid for the groceries so they couldn’t complain too bad. 

Dean made a noise of understanding. “Wanna go for dinner tomorrow? I can ask Cas if he’d be up for it.” 

“Wings?” 

“Done.” 

“Thanks chief,” the big guy said with a head nod. In his pocket his phone chimed and Benny checked it quick before giving Dean a guilty smile. “I gotta head out, Andrea wants to meet for food right now.” 

“Isn’t it weird for you?” Dean asked before he could help himself. 

“What?” 

He didn’t know what actually compelled him to ask the question aloud but now that he had, he realized how much he wanted to know the answer. “Is it weird to be friends with her after everything that happened? You two dated for like three years and now you’re just best friends like it’s nothing? How does that even work?” 

Benny gave him a weird look but answered it regardless. “We don’t really act like nothing happened, to be honest. We had a relationship, it was great and all for a while so yeah it was a little weird at first just being friends but now? I don’t know, brother. I just want her in my life but I don’t want to be with her and she feels the same.” 

“You really think you can be friends with an ex? Someone you’ve been… you know… _with_?”

“Lot’s of people are friends with exes. Just because you’ve hooked up doesn’t mean that friendship isn’t an option after that.”

Dean nodded, trying to feign some sort of understanding. “I guess I’ll just take your word for it.” 

“Is something up?” 

“Nah. I was just curious.” He brushed off, trying to quickly mask any sort of _‘I’m kind of sticking my dick in Cas’s face and am freaking out that we won’t be friends after this’_ that might have been evident on his face. 

If Benny believed Dean or not, he didn’t say, but another chime of his phone had him heading towards the door. 

“Alrighty then. See you tomorrow. Text me when you’re hungry.” 

“Later man,” Dean called out. He sighed to himself when he heard the door click shut. 

He was alone in the dorm and that meant he was alone with his thoughts and he was kind of freaking out. Just a little. 

He loved this new deal he and Cas had going for them and he was completely relieved that nothing felt awkward either They were as normal as ever, they still joked around, still worked on homework together, still watched the same lame TV and played video games. Nothing changed except now, Cas would ask Dean if he wouldn’t mind if he practiced his blowjob techniques on him in the middle of whatever they were watching. And it was so normal that it was making him wonder when the other shoe would drop. 

At some point the comfort would wane and he’d be left with an awkward mess where his friendship should be, right? Wasn’t that what every single movie about friends with benefits told them? It worried the shit out of him. 

Cas had been an instant part of his life and Dean dreaded that this arrangement would ultimately rip that from him. He knew people like Benny and Ash and even Victor were good friends to him but they didn’t get him on the same level that Cas did. They didn’t notice when he started to feel worn out from putting on his charismatic front. They didn’t understand that he hated when people tried to get too personal with him, asking him prying questions about what he was like as a kid. 

It was safer to keep a wall around himself. One that he only let his family into and that included Cas. And Cas understood that. Cas didn’t have much in the way of family so he understood why Dean would keep the people he cared about close and keep his heart even closer. 

What was going to happen if this whole situation blew up in his face and he lost the one person outside of his family who he managed to let in? 

He knew it was gonna hurt like a mother and Dean was scared out of his wits. But despite the rational solution being to stop while they were ahead, Dean kept telling himself that he made Cas a promise and he didn’t want to let his friend down. 

Speaking of. 

**Cas:** Leaving Hannah’s now 

**Cas:** Did you eat? 

_Me:_ No 

**Cas:** I have a burger and fries for you. They’re cold so I apologize. 

_Me:_ Thanks buddy

Benny said it could work though. It worked for him and Andrea and they’d even been engaged so there had to be a way for nothing to change between him and Cas when this was all over. 

He’d make damn sure of it.

* * *

Dean was currently flat on his back huffing up at the ceiling, willing his heart rate to go down because oh fuck… that was a good one. 

He’d have thought that after nearly two weeks of Cas giving him seemingly endless head that the orgasms wouldn’t be so intense but Cas was very keen on improving his technique, and he sure as hell had. 

It seemed somewhere in the last few days Cas had mostly gotten over his self-consciousness. At first he questioned everything, checking with Dean almost constantly if what he was doing was right or pleasurable. He’d also apologize profusely each time he tried to suck down more of Dean’s length and couldn’t help but induce his gag reflex. Each time Dean heard an apology slip from Cas’s lips Dean wanted to punch himself in the face.

He wanted to shower Cas with all the praise he could think of because Cas was a _fast_ learner and Dean was meant to be his teacher in all this and help him know that he was doing amazingly. It was just hard for him to get the words past his lips, but he vowed he’d try harder. 

Right then, Cas was still between his legs on the bed after climbing onto Dean’s bed that afternoon after Dean woke up from a nap, asking if he could practice again. He was currently staring at Dean as he came down like usual. It seemed to be something that Cas liked to do, watching Dean come down from an endorphin high. Dean supposes it made sense—he used to like seeing just how intensely he’d made his partners come; gave a person a bit of an ego stroke to know they did that. Like always, when Cas seemed satisfied with watching over Dean, he moved to pull away to clean up and like always Dean had to ask: 

“You need to get off? I don’t care if you stay out here.” 

It wasn’t surprising when Castiel responded with, “No. That’s alright. I’ll just go shower.” 

His same answer every time. 

It’s not that Dean necessarily wanted to watch Cas get himself off or something (maybe he was intrigued) but Dean had just been wondering why it was that Cas didn’t seem to bother to do it right away. Why was it always cleaning them up and _then_ taking care of himself in the shower? He knew that Cas got turned on by their arrangement (it was especially evident when he wore sweat pants) but he never seemed to act on his arousal right away. 

Dean didn’t mind if Cas wanted to do it in front of him. He wanted this to be a mutually beneficial deal and he felt increasingly more selfish each time Cas had to take care of himself in the bathroom while Dean got to bask in the afterglow of some pretty awesome orgasms. 

Perhaps it was his still bliss-hazy mind that had him speaking up this time, stopping Cas before he could climb off the bed. “Wait. Why do you always go do it in the shower? I told you, I really don’t mind if you do it out here.” 

For some reason the question made Cas a little shifty. “Uh, no reason.” 

Trapping his friend with his legs, Dean gave his best friend his best menacing look. Well, as much as he could with his lower half buck-naked. 

“Bull.” 

Cas adjusted himself just a little, clearly trying to hide his evident arousal. “I just… we didn’t agree on it.” 

“On what?” Dean asked, still keeping his legs around his friend. Cas wouldn’t look him in the eye. 

“It’s not about me.” 

“What do you mean?” 

Cas sighed heavily, looking like he was trying to find the right words. 

“We agreed to help me learn how to pleasure another person. I already know how to pleasure myself so there’s no reason for you to deal with that too.” 

A wild mix of thoughts and emotions swept through Dean and it took him a moment to shove them aside enough to focus on Cas. He hated that Cas thought this wasn’t about his pleasure too, and it made him feel disgusted with himself that he’d already let Cas spend weeks thinking that he was just there to get Dean off. He didn’t know how he was going to word it but he knew he needed Cas to understand that Dean wanted this to be as good for his friend as it was for himself. 

“I’m not cool with that,” is what came out of his mouth. 

Cas finally looked up at him, worry clear in his features. “What?” 

“This isn’t just about me, dude. It’s a two person deal and if you’re not enjoying yourself then maybe would shouldn’t…” he moved to pull his legs away and sit up but Cas’s palms landed on his shins, keeping him there. 

“I am enjoying myself.” Cas insisted, looking even more worried than before. 

Dean bit his lip as he tried to think of what to say. The thought of letting it go on the way they were wasn’t settling right with him. If he knew Cas saw this as a one-sided arrangement where Dean would get his rocks off and Cas would be exiled to the bathroom to get any pleasure, it wasn’t going to work. 

He wasn’t sure if he’d want to return any of the favors but he did know he wanted Cas to stick around, and he really, _really_ wasn’t opposed to being there if Cas got himself off right after. If Cas didn’t want him to watch, that was fine, but Dean didn’t want him leaving. 

“We uh—we said we’d tell each other if we didn’t like something and I uh—I don’t like this just being about me,” He explained. “You should be able to get off too, especially if you’re turned on by what we’re doing.” He backtracked then, realizing he’d been assuming Cas was even aroused by Dean. “You are turned on right? I mean I could always go into the bathroom while you watch something or do what you gotta do I just don’t want you thinking you have to leave right after because you don’t.” 

Cas’s face relaxed significantly, a near smile gracing the edges of his lips. 

“I am turned on by it,” he admitted. “I am.” 

He felt relief wash over him hearing that and seeing Cas more relaxed. 

“Then you should feel good from it too.” 

Dean could tell Cas was mulling it over for a minute before he said, “I’ve never, uhm, I’ve never masturbated in front of another person.” 

“That’s okay,” Dean ensured despite the fact that his insides felt a little warm at the thought—he ignored them for now, choosing to focus on Cas’s needs. “Do you want to try?” 

“Right now?” 

“Why not?” Dean shrugged but Cas frowned and looked down at his own crotch. 

“I’m not fully…” 

“Oh,” is all Dean could say. He felt stupid for talking so much that Cas didn’t even get to enjoy getting off. He wanted to apologize but Cas was talking before he could manage. 

“Uhm I think I could, you know, try again?” 

Cas looked nervous but Dean was already nodding his head. 

“Yeah, you should.” 

“Okay.” 

They stared at each other for a while, both a little unsure where they should start. It dawned on Dean that Cas was looking for his cues, because Dean was supposedly the more experienced one and was supposed to teach the other man how to do all this. Only, for some reason, Dean felt new to all this too. 

“How do you want to?” He asked. “My bed? Your bed? Do you want me to leave?” 

“No. No, you can stay.” Cas said quickly. He appeared to be looking around the room and their current situation on Dean’s twin bed. “Uhm, can I stay here?” 

“Yeah, yeah, that’s fine.” He only just realized that he was still naked from the waist down and his leg was still draped over Cas’s lap. He quickly shuffled himself to sit up against the headboard and pulled the corner of his comforter over his lap. Not really knowing what Cas wanted from this, he had to ask, “Do you want me next to you? Or like at the end of the bed? Or like you leaning against me or something?” 

He wished he could read Cas’s mind right then because his friend looked an equal mix of terrified and amused. Dean also really hoped that the color showing up in Cas’s cheeks was from arousal and not from embarrassment. 

Cas swallowed hard before saying, “Maybe, maybe leaning on you?” 

“Yeah, yeah. How about you sit between my legs,” Dean suggested, before he could stop himself. 

“Okay.” 

Cas started to awkwardly scoot over towards where Dean was sitting and Dean felt compelled to ask, “You okay?” 

“I’m nervous,” his friend admitted easily and Dean couldn’t really blame him. 

He tried to be reassuring as he said, “That’s okay, I’m gonna help you.” 

“Dean, no. I can’t ask that of you.” The dumbfounded look on Cas’s face was enough to make Dean realized what it sounded like he was offering. 

“I’m not gonna jack you or anything, I just want to help you keep in the right head place.” 

“Wouldn’t that be—Isn’t that weird for you?” 

“No weirder than you sucking my dick every day. So get over here, pants off, your back to my chest.” He knew he sounded more confident than he felt but he wanted Cas to be comfortable enough with him to do this. He waited with almost bated breath as Cas started to strip out of his pants. He tried not to look at his friend’s dick but… he was curious alright? 

When Cas finally crawled back onto the bed and moved between his legs, Dean wondered if this was a horrible idea…. But it was too late now. He’d already committed. He shifted just a little to make sure nothing was accidently rubbing up against his best friend before pulling Cas’s back solidly against his chest. “Comfy?” 

“Yeah.” Cas said with a trembling voice. 

Careful to keep his hands solidly on his own thighs, Dean figured it was now or never. “Okay, show me what you do.” He commanded, though is sounded a little shaky to his own ears. 

“Dean…” 

He could feel Cas’s nerves from the whole situation and he hoped that his own weren’t showing but he wanted to do this for Cas. The whole point of this arrangement was to help Castiel feel more confident in himself as a sexual being and Dean could at least do this for him! He just needed to offer a little encouragement. 

“Dude, you’ve seen my dick up close and personal for the past few weeks, there is nothing to be embarrassed about. And as far as dicks go, you’ve got a decent one.” He commented plainly. It wasn’t like it was a weird thing to tell his friend he had a nice cock. It was just a gesture to help his friend out. That’s all. 

Still Castiel didn’t seem eager to get on with it even though his dick was twitching in a way that said otherwise. 

“Dean, really, I can just handle this in the shower, it’s not a big deal.” It was the half-hearted argument that had Dean growing a little more stubborn. Cas seemed to want to do this—so Dean was sure as hell going to help him out. He tried to quickly think of ways he could make this a good experience for Cas, without touching him like that. Praying that he wasn’t wrong, he hoped that his voice could be considered sexy if he lowered it enough, so he chanced that maybe it’d work for Cas if he whispered against the ear near his mouth. 

“Touch yourself.” 

It was the shaky gasp that told Dean it’d worked and he almost melted in relief but was too distracted by the fact that Cas started to stroke himself almost instantly. He tried not to watch too intently, not really sure if he should but after a few moments of Cas’s breath staying even Dean had his eyes locked intently on the dick pushing in and out of his friend’s fist. It didn’t look particularly stimulating and Dean wasn’t sure if this was Cas’s usual method or if he was just a little trigger shy from Dean watching. 

Regardless, Dean wanted his friend to be confident with this—some people got off watching their partners take care of themselves so this was something Dean felt Cas should learn. When he couldn’t take watching Cas half-heartedly stroking himself, he snatched Cas’s wrist in his own hand and brought his palm to his friend’s lips. “Lick.” 

Obediently as ever, Cas did as asked making sure to get his palm thoroughly wet before bringing it back down to continue his touches. He seemed reserved still… in a way that was starting to make Dean wonder if he’d broken a rule and pushed Cas to do something he really didn’t want to do. Should he have just let Cas take care of himself in the shower? 

“Could you… could you tell me where your mind is at right now? I’m starting to worry that I’m making you do something you don’t want to do.” Cas’s hand stopped moving as he tried to look over his shoulder at Dean. 

“No! Dean, no, that’s not at all it. I just… I don’t want to keep you here for too long… and this wasn’t part of our deal and you don’t need to help me. It’s supposed to be about me pleasuring you.” 

“No it isn’t. Cas, our agreement is for me to teach you how to pleasure a partner. And believe it or not, buddy, most people think it’s hot as fuck to watch their partners get themselves off. So just think of this as another learning experience… you do this confidently and you’re going to have whoever you’re with coming in their pants.” 

“Really?” Cas asked skeptically. 

“Take my word for it.” He couldn’t bring himself to divulge his entire thought because he didn’t know quite the right way to say that even he found the idea of Cas getting off a little arousing if not for the sole reason that Dean wanted to see his friend as satisfied as Dean has been. 

“I don’t have to be here though… I could do this on my bed if you’d rather have some space.” 

“Stop. That’s not a sexy thought. I really don’t mind. Just, stop overthinking this okay?” He didn’t like that Cas’s self-consciousness was peeking through. Dean knew it was his fault again. He just threw Cas into an awkward situation and was doing nothing to guide him along. He needed to step up to the plate. “What turns you on?” 

“I don’t know.” 

“You do… you do know what turns you on.” 

“I like…” The words seemed to not want to come out. “I, uhm, I like…” 

“Tell me,” Dean whispered again in his ear making Cas shiver, he knew he’d remember this little trick for the future if he got the chance. 

Cas’s response came out in a rush. 

“I like the noises you make.” 

Dean couldn’t help but smirk a little. Who didn’t have a sex noise kink? It was always so thrilling to hear the way you were making someone feel. Now it was Dean’s turn to try and drive some of those same noises out of Cas. Knowing he wasn’t brave enough to use his hands, he worked with the only tool he had: his voice. 

“Yeah? You like hearing me?” He could feel Cas shaking against him and hoped to all things mighty this was working. 

“Yes.” 

“Do you know how good it feels when your mouth is on me?” 

“Dean…” 

“There you go, keep going.” He felt Cas press more firmly against his chest, as his friend’s hand started moving steadily more quickly. Something about this made Dean feel more bold, and the praise he’d been too shy to give his friend came pouring out. “You’ve been so good at all of this, you know? Every single time it’s so good. Fuck. I had no clue how awesome it’d be when we started. It takes everything in my to hold back.”

“Mmm.” 

There it was. That’s what he was looking for. 

“There you go. Does it feel good?”

“Yes.” 

Dean felt his hands twitching. He didn’t know what came over him but suddenly he felt this undeniable desire to touch. He kept himself in check fisting the blanket around his hips while he as Cas’s orgasm started to creep up on him.

“Dean…” 

“That’s it. Don’t stop. Are you close?” 

“Mm.” 

Cas’s head leaned back onto Dean’s shoulder as he panted into the air above him and Dean couldn’t keep himself from not touching. He wrapped one arm around Cas’s waist as the other pressed into Cas’s chest, keeping him firmly against Dean’s chest. 

“It’s gonna feel so good. Come on.” 

“Dean…” 

He could feel Cas quivering against him. Could see his friend’s toes curling near the edge of the bed. Dean’s own body felt like it was building up too. “That’s it. Don’t hold back.”

Hardly a beat later Cas’s head pressed firmly back against Dean’s shoulder as his body began spasming with his release. Dean’s arms held him tightly, keeping him from writhing too hard. “That’s it. So good. That was so good,” he babbled into Cas’s hair. 

After a while, Cas’s spasms slowly died down to trembles. Though Dean had never seen his best friend come before, he figured it was safe to bet that that had been an intense one. So, he had no problem allowing Cas to rest up against him until his limbs came back to life. 

Dean’s dick was one hundred percent back in the game so he skillfully tried to keep his pelvis angled away from the small of his best friend’s back while he waited. 

“That… that was…” Cas let his voice taper off into some mild pants, still trying to connect his mind to this mouth. It made Dean smirk in satisfaction. 

“Really fucking good, huh? How do you feel?” 

“I didn’t know it could be so… intense?” 

He had to admit that he felt a little proud that he was able to assist in getting his best friend to feel that level of pleasure. 

“Never felt like that before?” 

“Not even close.” 

“Now you know what you’ve been missing out on. It should always be like that.” 

“Always?” The awed wonder in Cas’s voice had Dean chuckling a little. 

“Mostly. If you’re doing it right.” He couldn’t bring himself to lie to his friend, even sarcastically, because the guy obviously knew first hand that not all orgasms were quite as earth shattering.

They settled on the bed a little, almost in some semblance of a cuddle before Cas finally sat up. He angled himself off the bed a little before turning to Dean with a grateful look on his face. 

“Thank you, for that.” 

“It’s what I’m here for.” Dean shrugged off. Cas still had a penchant for thanking him for their arrangement and Dean didn’t want to always shut him down for it. “You wanted to learn these things so I’m here to help.” 

“Would you like me to take care of yours?” 

Cas’s eyes lowered until they focused on the obvious tent of the sheets were Dean’s dick was fighting to be seen. A very selfish part of Dean wanted to scream yes because he knew just how good it would feel to get Cas’s mouth on him two times in one day but a bigger part of him couldn’t bring himself to be that kind of guy. 

“Nah. I got it. Thank you though.” 

Dean finally allowed Cas to get up from the bed with a teasing appreciative whistle that had Cas blushing just enough. 

As Cas was making his way to the bathroom Dean called out, “Are we still meeting Benny for dinner?” 

“Yeah. Mind if I shower first?” 

“Go for it.” Dean responded happily. 

He’d never admit to watching his best friend’s naked ass walk towards the bathroom or that fact that he came in under a minute once the door had shut. 

Nope. Didn’t happen.

* * *

Sunday found Dean sitting on Benny’s couch with his friend and Ash and a few other of their mutual friends watching the game. He had to laugh a little to himself because in the past few months he’d seen his friends less than he had in this entire weekend. It was nice that he was getting out of his dorm and being fed food he didn’t have to pay for but Cas was still stuck at the dorm since he had an assignment due that night for his creative writing class and he’d effectively kicked Dean out even though Dean usually didn’t like to be out of the dorm on Sundays. Apparently he was a _distraction_

With half of his attention on the game and half of his attention on the meat lover’s pizza he was cramming in his face, Dean tried to pretend like he wasn’t wishing he were in the comfort of his own rickety futon. He really just couldn’t get into the game, which was the whole point of coming over to Benny’s since the other guys were constantly hooting and hollering when things went their way. Dean didn’t have any particular team he was rooting for and really when it came to sports, he only rooted for the Cowboys just because he knew it pissed Bobby off more than anything. There was nothing funnier than seeing the man turn bright red while he talked about the Texas team. But here, these were two teams that he could possibly only name their quarterback just because the guys in the house were referring to the players as if they were old friends. 

In sum he was pretty bored. It was nice chatting with his friends and seeing Ash get progressively more stoned as the night wore on but if Dean were being honest with himself he couldn’t stop thinking back to his dorm. At least there he and Cas could watch something that interested both of them. At this point he’d even go for watching the one documentary about some girl who was shot in the face but lived to fight for education… he couldn’t remember the name but Cas had talked about the girl for days, detailing on and on about how influential she was. (Dean asked him to wait to watch the documentary together). 

It was a relief when he saw Cas’s name on his phone. He told his friend to text when he finished to see if Dean were still at Benny’s to have Cas come over. Having Cas around might make the evening more fun. At least Cas could add in his friggin’ hilarious voice dubs for the events happening in the game. It was a running joke that Cas would lean over to Dean and start making hysterical dialogue for what the players were saying on the field. It made Dean nearly piss himself every time. 

**Cas:** My assignment is finished. 

_Me:_ Come finish the game at Bennys 

**Cas:** I was thinking we could you know… ? 

Dean nearly choked on his pizza and tried to play it off cool despite a few weird looks from the guys. 

Quickly he typed out: 

_Me:_ On my way 

He was only a little ashamed he let his dick take the driver seat in replying to Cas. He practically jumped off the couch in his haste to get out of this house and back to where an insanely amazing blowjob was awaiting. 

“Hey guys. I’m gonna head out.” 

“The game’s not even over!” Benny protested, eyes still glued to the game. 

“I know but I just remembered I have homework due for my morning class that I haven’t even started.” 

There was collective booing from all the guys that Dean handled with a very sophisticated middle finger in the air. 

“Dumbass. Get outta here.” Ash called after him when Dean’s hand signal was met with a matching pair in the air. 

“Let me know if you want to hang out sometime this week.” He called out to all of them, mostly as a formality. 

“Later Winchester!” 

He tried to not allow himself to run back to the dorm but his limbs were without a doubt taking him across campus at a much faster pace than his usual stride would. He had to admit that there was something thrilling about the fact that Cas had _texted_ him to get some “learning” in. Something about the possibilities of what he’d walk into… would Cas be eagerly awaiting him? Would he want to do this quick and dirty or would he want to draw it out? His friend had definitely been having fun with trying to draw out the buildup lately so Dean had a feeling he’d be up for a little of that at the moment. 

But whatever Cas might have been planning suddenly was pushed to the backburner when Dean walked into their room. Dean watched his friend hop up from the couch, his hand flying away from where it had obviously been down the front of his pants and suddenly Dean was filled with inspiration. 

He strode across the room with more confidence than he was actually feeling because deep down he wasn’t one hundred percent sure Cas would be up for this, but of course he’d give him the option to back out. He wagered Cas would like it though. 

“Take your pants off.” Dean requested in a low voice. 

“What?” Cas stammered. 

“Take your pants off.” Dean said once more, twisting his voice to the same cadence he’d whispered in Cas’s ear a few days prior. It was then that Cas’s eyes widened in intrigue, like he understood that something awesome was going to take place. In a matter of some clumsy minutes later Cas was bare from the waist down. “Touch yourself.” Dean commanded next, watching as Cas’s hand instantly wrapped around himself. “You up for trying something?” 

Cas looked a little unsure for a moment before he nodded his head. 

“You cool with being on your knees?” 

“Yeah,” his friend said breathily. 

“Okay, on your knees, but don’t stop touching yourself, alright?” 

With the sight of his best friend falling down to his knees, Dean instantly started fumbling with his belt and tugging his pants all the way off until his bottom half was left bare. He was without a doubt already hard so it didn’t take more than a few satisfying strokes to know he wasn’t going to last more than a minute. 

“It you don’t like this or your knees or neck start to hurt, just tell me, okay?” 

Something about those blue eyes peering up at him made Dean feel a little weak in the knees but he steadied himself with a few breaths. 

“I will,” Cas promised, voice like gravel. His lips parted, inviting Dean to trace the head of his cock against them and Dean didn’t resist the pleased sound that escaped him. Cas’s hand suddenly rested warmly at Dean’s hip, steadying himself, but flew back down to his lap when Dean looked down at him. 

“No, it’s alright. You can touch me just don’t stop touching yourself either.”

Cas’s breathing stuttered a little. “Okay.” 

“Good.” 

Cas wasted no time then opening his mouth and taking Dean in. Wanting to let Cas take this at his own speed, Dean settled his hands gently on the sides of Cas’s head, loose enough that they were barely touching. 

It was still slightly terrifying to know that he wasn’t just getting head from anyone but from the person he called his best friend. Even so, as each day went on and Cas showed more enthusiasm for perfecting his technique, Dean couldn’t help but let his self-consciousness fizzle out. He felt emboldened enough to let out all the sounds he’d been holding back with Cas, now having also verbal affirmation that Cas wasn’t put off by his sighs of pleasure. This time, Cas’s own moans matched his own. Dean couldn’t help but sneak a glance down at the other man, whose eyes were now locked on his. Looking further, Dean could see Cas’s hand moving rapidly over his aching erection and he was certain Cas had to be close. 

“Does this turn you on?” He asked aloud. 

All Cas could do was moan as he tried to frantically nod his head with a mouth full of Dean. 

“You’re so fucking good at this. Feels so good,” his words were breathy but holy fuck did it feel good. 

It was evident enough that Cas was really into this too and Dean didn’t know if he could pry his eyes away from the sight if he tried. 

It might’ve been a little sloppier than some of the other times Cas had sucked him but seeing Cas looking up at him and hearing his friend’s own pleasured sounds were sending him racing to the edge. 

Right as he was about to tell Cas to pull off, his friend’s eyes screwed shut as his orgasm washed over him, and that sight did nothing to help Dean stave on his own. Not thinking, he reflexively gripped Cas’s hair tightly and pulsed down his friend’s throat until he had nothing left to give. 

_Holyfuckholyfuckholyfuckthatwasgood._

Weakly, he sank down on the futon as he attempted to catch his breath. He didn’t care that he was butt ass naked on the couch, nor did he care to try and have some decorum and cover himself. Instead he just turned his head toward the man he called his best friend. Cas looked a little wobbly as he tried to get up off the floor. 

“Come here.” Dean called out, voice a little hoarse from usage. 

“I should clean up.” He protested, his knees popping a little as he stood. 

“I said come here.” Dean countered, reaching his arm out to lightly grip Cas’s wrist. 

“But we’re a mess,” Cas gestured, mostly to himself. Dean flicked Cas’s sweats from up off the ground and told him to use that before tugging on his arm to get him onto the couch. 

Dean kicked his legs up onto the ottoman as Cas settled into Dean’s side, turning his body just enough to rest his cheek on Dean’s shoulder. Without hesitation Dean enclosed his arms around his friend’s shoulders, and waited for Cas’s arm to drape over his waist before speaking. “Are you okay?” 

“Of course.” 

“That was…” He didn’t know where to start. _Fucking amazing and what my spank bank will probably have on replay for years to come._ Fuck. 

Now that his imminent need for release had been quenched, Dean’s mind started to circle with thoughts on how much just happened between them.

“Hey, I’m—I’m sorry for not telling you when I was going to come, I should’ve—” 

“No, it’s okay, really. I think liked it,” Cas’s tone left no room for lies which was a relief and let Dean’s praise come out easier. 

“That was really good. Like really fucking good.” 

“It was?” 

“Did you—did you like it? Being able to get off at the same time?” As much as Dean wanted to see Cas’s eyes when he answered, there was still something inside of him that couldn’t bring himself to peer down at his friend when they laid like this. Some line between too intimate and too… _something_ always stopped him. 

Cas didn’t seem to mind the lack of eye contact at these times. “I did. A lot.” 

“I think it’s safe to say you’ve officially graduated from Blow Job University.” 

There was a bittersweet, but mostly bitter, feeling deep in his chest as the words fell from his lips yet there was no way to deny their truth. Castiel had asked for assistance with hand jobs and blow jobs and Dean knew there were only so many ways the other guy could suck his cock before Dean ran out of things to “teach.” It decidedly meant that their arrangement was coming to an end and Castiel could go off and put his new skills to whatever use he saw fit. 

Dean didn’t have to like it but he would be resolute that his distaste came from the lack of ‘free head’ he’d be getting… that was surely all it was. And no, there was no reason that a wave of relief rushed through him when Cas hesitantly spoke into the silence between them. 

“I should really get my Masters though, don’t you think?” 

He laughed in lieu of revealing just how much he found comfort in those words. 

“I’m sure there are a few more courses you could take.”

**Notes for the Chapter:**

> Was that awkward? I kinda hope the awkward paid off but wasn't TOO awkward. The initial draft of this was a little less awkward but I felt that the original version made them both too confident in their new arrangement so I had to switch some things up. 
> 
> I'm so glad people seem to like how caring Dean is in this one. I love writing him that way :)


	5. October, 2017

**Notes for the Chapter:**

> I'm sorry for not having this up earlier. I was out of town without internet and then severely underestimated how much I'd want to edit. The next one should be up Saturday or Sunday :)

“I think I managed a butt dial successfully this weekend.” 

Castiel waited patiently as Hannah took a moment to compose herself after choking on her coffee. He knew by her reaction alone he hadn’t worded that correctly. When she seemed finally able to breathe correctly again, the look on his friend’s face was beyond confusion, confirming his thoughts. 

“How can you butt dial someone successfully?” She was already giggling around her coffee cup, he light blue eyes shining with amusement. 

He glared at her as he explained, “I asked… the guy I’m seeing to come back to my dorm so I could perform oral on him.” 

His words came out carefully, ensuring he didn’t slip up and say too much. 

He’d tried so hard to keep his and Dean’s arrangement to himself. He knew it was no one’s business but his and Dean’s and he wanted to stick by that belief but he didn’t realize how hard it would be to keep it from his best friend. 

At first he felt like he did a good job keeping it from Hannah, but seeing her as often as he did, she started to notice that he was acting weird and pestered him long enough to get him to confess. _Sort of._

He’d told her the best half-truth he could think of and hoped she’d accept it. 

He said he’d met a guy from the university, at a bar, on a Sunday and decided to work out an agreement to mess around. Casual. Nothing that required his best friend to know the guy’s name and Facebook stalk him because Cas didn’t think it warranted it. 

He must have done a fairly impressive _‘I’m not going to budge on this’_ face because Hannah didn’t question it further and just asked Castiel if he wanted to talk about it. Which he did, immensely. Now whenever they met up, which was often, he’d take some time to update her on his ‘hook ups.’

“Oh god, Castiel. That’s called a booty call not a butt dial.” She hid her face in her hands, messing up her bangs as she laughed into her palms. 

“They’re different?” 

“I truly hope you’ve never accidently butt dialed someone before and apologized for booty calling them.” 

“It would explain why my dad laughed at me once…” Damn his father for thinking it would be _hilarious_ to teach Cas to say common phrases, slang words, or idioms wrong. 

He will still never recover from the time he’d told his debate teacher in high school that he wanted to go home and “hit my sack,” because he was so stressed. The detention mixed with the few teases from some of his friends who’d overheard led to one of the first few times he’d been angry with his dad. After that he was much more conscious about saying things incorrectly. He was getting better with Hannah and Dean’s help, but it was a slow process. 

“You’re helpless,” Hannah laughed with him. “Anyway, tell me what happened with him. Wait. Was Dean at home?” 

She wasn’t making it easy for him, keeping this secret, since every time he mentioned hooking up with his mystery man, she was always so concerned about Dean’s whereabouts. He’d told her he’d been keeping it a secret from Dean too in hopes that she’d never ask the other man about it, but because of that she seemed to want to double check that Cas was doing a good job of keeping the secret from him. 

“Dean? No-No. Dean was at Benny’s so he… he wasn’t there,” he fumbled to explain, taking a big drink of his coffee before caring on. “And the guy left before Dean came home. Way before.” 

Hannah seemed accepting of his mumbling and merely took to sipping her coffee again and waiting for Castiel to talk and explain what had happened. It was still a little awkward trying to explain his sex life, since he kind of had one now, and didn’t really know what was custom when engaging in those conversations. 

“Uh, do you still wish for me to refrain from details?” he asked, knowing the first time he went a little too in depth with his descriptions of tastes and sensations. 

Hannah pushed her bangs out of her eyes and propped her chin and her fist. “Yes, please,” she requested, with curiosity. 

It took him a little to find out how to say what happened without being explicit. 

“It was pretty quick really,” Cas supplied. “He got to the dorm and it was… different than usual but good different. I really enjoyed it.” 

Despite Hannah being more reserved and conservative when it came to her own sex life, she was very supportive in Castiel’s own curiosities which he was immensely grateful for. She listened to anything he had to say with rapt attention and gave him advice whenever he asked for it. 

Right now though, the crease between her brows was concerning. He wasn’t certain what she was going to say but he knew that he feared that she’d someday express disappointment in him, or judge him for what he was doing. 

“You’re happy? With how things are going,” she asked. He could feel her scrutinizing him for any signs of discomfort but he was pleased he could answer her honestly. 

“I really am,” he promised. “I believe he is as well.” 

He didn’t explain to Hannah that things were going much smoother than he’d ever anticipated. In fact, he’d been certain that Dean was going to freak out over the whole thing and that their friendship was going to crumble yet, that wasn’t the case. Dean was encouraging and helpful and just so _normal_ about all of it, but it didn’t make sense to him. 

He knew Dean was straight and that his best friend had only ever been with women and would only ever want to be with them in the future. He was well aware that Dean was just doing him a favor and that the arousal Dean felt was only due to the fact that he was getting oral sex regularly and had nothing to do with Castiel himself. He just didn’t expect to feel like Dean was kind of enjoying himself and seemed to want to help Cas but he wasn’t going to complain. 

He _might_ let the noises Dean makes get to him too much and maybe in those brief moments where Dean pulls him into a cuddle, Castiel fantasizes what it would be like if it were all real. He knew it was dangerous to let his thoughts wander away like that but he couldn’t help it. What would it feel like if Dean pulled Cas into his arms because he wanted to, not because he felt responsible for Cas’s wellbeing? What would it feel like if Dean touched him more than just hesitantly, or said Castiel’s name in the midst of his pleasure? He didn’t even know what he would do if he ever heard Dean moan his name and had verbal proof that his own body was the cause of Dean’s pleasure… 

It didn’t do well to settle on fantasies though. 

Castiel knew he had to pull himself back to reality each and every time. Dean was his best friend who was helping him out because that was the type of man Dean Winchester was. Dean Winchester could never and would never feel anything more for him than just friendship and Castiel was perfectly content with that. 

As if Hannah could sense his train of thought, she asked the one question Castiel had been training himself to side-step around quickly. “Do you think... would you want to make it become more?” 

He kept his features as even-keeled as possible, knowing exactly what she was asking but not wanting to answer her question. He knew she’d been itching to ask him if he had an interest in forming a relationship with this stranger she’d never met but he didn’t want to completely lie to her. He also didn’t want to allow himself time to think about being in a relationship with someone he’d never have. 

“I am curious about intercourse,” he stated, because it was true and knew it technically answered the question that came out of her mouth. He was fine with playing naïve. “I just don’t know how he would feel. I’ve been considering bringing it up soon though. Intercourse would be the next logical step and I’m unsure if there is really any more I can learn through oral.” 

“Oh.” 

Hannah’s face dropped for a moment and Castiel wondered if he’d said something wrong. She looked upset or worried as she asked, “You think you’d want to actually go all the way with him?” 

He hadn’t really thought much past trying to side step her initial question so it came as a shock to realize he wasn’t sure if he wanted to answer this one either. 

He hadn’t lied when he said he thought it would be the next logical step. It had crossed his mind many, many times that he was weighing the pros and cons of at least asking Dean. 

Just the thought of maybe being that intimate with his friend, to cross that specific line sent a thrill down his spine. 

He’d never admit it to Hannah, or to anyone really, but now that his orgasms were far more regular than ever, he swore his fantasies were getting more and more intense. Now, in the few and far between times Castiel was left in their dorm while Dean was attending his classes or with friends, Castiel found himself with his hand around his dick and his mind racing with thoughts of what it would feel like to have Dean’s mouth all over his body and the beautiful cock he’d become so familiar with inside of him. 

He wanted it so badly yet he didn’t know what to do about it. He knew Dean had only agreed to receive a few hand jobs and a stream of blowjobs from Cas but now what? Every time Cas had to think about putting an end to his ‘learning’ with Dean, dread would overwhelm him. He couldn’t stand the thought of not getting to have these moments anymore. Without the romance, without the relationship, they were still intimate moments between himself and Dean. He hated that once this was all over that Dean would likely go out into the world and have these types of moments with random girls again. 

Castiel wanted to keep him all to himself. 

He knew it was selfish. He knew he had no right to Dean and no hold over the other man but every time he got to see Dean naked, every time he got to touch Dean’s skin, every time he was the one who pulled an orgasm out of his best friend, Castiel couldn’t help but feel more and more needy. He knew it was wrong of him to not put an end to their arrangement. He knew that growing these feelings was crossing some sort of line, but he couldn’t help himself. 

He was selfish when it came to Dean and he wanted more. But what more could Cas offer him if not intercourse?

“It’s been nearly a month since our arrangement has started, it seems like the next course of action, don’t you agree?” Castiel asked, hoping his silence hadn’t given away any of his useless thoughts. 

Hannah frowned. “I guess? It’s different for everyone.”

He could tell something was bothering her. “What is it?” he asked. 

“May I be honest with you?” 

The lack of eye contact Hannah offered him at the moment unnerved Castiel slightly. “You know you may, always.” 

It took her a while to start speaking and Castiel felt more and more unnerved with every moment. 

“I worry that you might be rushing into things too quickly,” she finally confessed. “I understand that it might be new and exciting for you but having sex is a big deal.” Picking at the sticker on her coffee cup, she took a deep breath and looked Cas in the eye, emotion heavy in them. 

“I—I haven’t told you this before because I hate to talk about it but… my—my first time wasn’t the greatest. It was with a guy I thought I was in love with and I honestly regret that it happened. I was so into him that I convinced myself he’d love me back if I gave that part of myself to him and that’s not at all how it worked out. I just—I just don’t want you to make the same mistake. You don’t owe him anything just because it’s been a month. You should do it only if it feels right and it’s truly what you want.” 

Reacting, he reached out and gripped her hand, wanting to provide her with whatever comfort her could offer from the opposite side of the table. He wanted to ask her a million questions and hear her open up to him about this but he knew from the sadness in her eyes that this was all she was willing to offer him today. 

He was touched that she’d wanted to confide in him and that she cared enough about him to look out for his own heart. She was a wonderful friend and one of the very best humans he knew and it made him angry to know someone had not treated her as wonderfully as she deserved but he couldn’t see the same thing happening to him, not with Dean. 

Maybe he was blind because of his feelings for Dean but he truly meant it when he said, “It is what I want and I… I really don’t believe he’d ever hurt me.” 

“Everyone who’s been hurt has said those exact words, Castiel.”

He knew she had a point yet he found himself thinking back to the way Dean always asked if Cas was okay… the way Dean pulled him close when they cuddled and made sure Cas was content. How could his friend who cared so much about his feelings hurt him? No, Castiel was sure Dean wouldn’t be the one to hurt him.

“I trust him,” he insisted, looking deeply into his friend’s eyes and pouring every ounce of honesty into his words. 

She nodded but seemed to remain skeptical, but it was Castiel’s fault she was in the dark towards the kind of man this ‘mystery guy’ really was. 

“Then I truly hope it works out for you,” she added. 

“Thank you.” He wanted to get the look of apprehension off of Hannah’s face and ease all her worries but as badly as he wanted to tell Hannah everything, explain to her all his thoughts and feelings, he’d made a promise to Dean and he’d never break it. 

“Enough about me. How was your midterm?” 

With grace, Hannah accepted his change in topic and indulged him. Yet it didn’t make his mind cease from drifting to her earlier concerns. Could Hannah have a point? He knew she was just looking out for him but he couldn’t help but wonder if she knew something that Castiel didn’t know. Was he being naive about all of this? Was Dean actually going to hurt him? 

His gut said no way but maybe his feelings were getting in the way. But when all was said and done, he understood that his and Dean’s arrangement would have to come to an end. He wouldn’t end up _hurt_ over it since he knew what he was getting into from the beginning. 

And even though Hannah seemed to think that “going all the way” would make everything hurt more for Castiel somehow… he couldn’t find it in himself to agree with her. Sex didn’t make people grow that much more attached to people, did it? Surely people had casual sex all the time… there had to be other people in the world who lost their virginities to people and didn’t grow insurmountably attached to their sexual partners. 

He’d be fine. 

He would just figure it all out for himself, thank you very much. He was a big boy after all.

* * *

“You can’t be serious.” 

“I’m perfectly serious.” Cas declared, ignoring the look on Dean’s face. 

“You’re trying to tell me you think that freaking little green Martians are more possible than ghosts?” 

“Although Hollywood has depicted aliens as such, I do not think that all aliens are green.” 

It was always a good time when he and Dean bantered about random things and tried to beat one another in a debate. More often than not they pretended to not see the other’s point of view just to rile the other up and make the argument more heated. Why they did it, he had no clue, but it always put a smile on Dean’s face. 

“Seriously Cas, you believe in aliens?” 

“I believe in the possibility that there is life outside of just our earth. Look at the universe, it’s seemingly infinite and yet we think that our planet is the only one in the entirety space capable of sustaining any form of life? Perhaps we could have the most sophisticated life form but even something as small as algae or bacteria on another planet would be proof of alien life.” 

“But ghosts could be real too,” Dean insisted, sipping at a beer they’d had hidden in the back of this mini fridge. 

“How so?” He challenged, wanting to listen to any and everything Dean had to say. 

Dean had a freakish obsession with horror films and ghost shows so much so that Cas often found his friend spending hours watching ghost conspiracies and other videos on the Internet or on Netflix. Cas himself didn’t think that paranormal activity was real but he didn’t outright think it was impossible. Dean however could go on and on about it and had some very valid points about sprit activity but often deflected to jokes and hoaxes as his proof to get a good laugh out of someone. Dean was so much smarter than he let others believe. 

“Everyone has a soul or whatever you want to call it and I just don’t get where it goes when we die? Isn’t it possible that it gets released into the universe once we die? Like where do our souls go? I can’t believe that people just stop existing once it’s lights out.” 

He relaxed back into his beanbag. “I agree that their energy is released into the universe but there is no quantifiable evidence for the existence of ghosts or spirits.” 

“Yeah? Then how do Ghostfacers get all those recordings of spirits talking back to them?” 

Cas let out a laugh. “Really? You’re sighting Ghostfacers as your source?” 

“Hey, they’re legit and you know it.” 

“They’re a group of man-children who run around screaming in a camera.” 

Dean didn’t even try and deny Cas’s assessment of the TV show group Dean was so obsessed with, instead he threw a pillow at Cas and shouted, “But they have proof of ghosts!” 

“They have audio tapes and records, yes, but how can we know for certain they were not fabricated or tampered with for views?” 

“Harry and Ed would never.” Dean growled, though his eyes were bright with mirth. He never really wanted to go into a real debate, just enough to get his friends laughing though Cas would love to pick Dean’s brain as much as he could if he were given the chance. 

“You’re never going to admit that you have no real evidence on the matter, are you?” Cas teased, earning him a confident smirk from the other man. 

“Nope.” 

“It’s like talking to a child.” 

“You’re a child.” Dean mocked back. 

“I’m done. I can’t take this anymore.” Cas threw his hands up and got off the couch, pretending to start packing a few of his belongings into a backpack. He could hear Dean laughing from the other side of the room. “He looks like a full-grown man but he’s really a six-year-old. I can’t do it,” Cas said to himself loudly, wanting to hear Dean’s laugh even more. 

“Well fine,” Dean cut in, sounding even more like a snobby kid. “Since kids don’t share, you can go down to the dining hall for dinner and I’ll eat the pizza when it gets here. I heard they have sloppy Joes and Brussels sprouts tonight.” 

“For your information I enjoy vegetables.” Cas pointed out. 

“Freak.” 

“You can suck your own dick tonight.” 

Dean barked out a laugh and then clasped his hands together, pretending to be begging for forgiveness. “I’m sorry. You’re a wonderful human and you are always right. If you’d like to have the larger slices of pizza, I’d be more than happy to serve those to you. Would you like a beer as well? Or would you like me to run down to the corner store and get you your weird ass green tea? I’ll do anything.” 

Cas appeared to contemplate for a moment before he leveled Dean with a smirk. “I did notice there was one more slice of that chocolate peanut butter pie Hannah made. I think I’d like that tonight.” 

“Yeah, your mouth ain’t that good.” Dean deadpanned as he sat himself more comfortably on the futon and pretended to dust himself off. He turned towards the TV and kicked his feet up on the ottoman once he was seated. “I’ll take care of my own dick, thanks. You just stay away from my pie.” 

The glint in Dean’s eyes when he looked over his shoulder had Cas laughing until his belly hurt. 

Two entire pizza’s eaten that night made no one feel very sexy so no dicks were sucked but Dean did share half of his pie with Castiel that night anyway.

* * *

Castiel woke slowly. It was Friday and there was no immediate need for getting up and getting ready for classes. The curtains were drawn so it was still mostly grey in the room aside from the orange glow of light coming from behind the drapes. He rolled over to his side and checked his phone and replied back to a few memes Hannah had sent him in the night before chucking it somewhere in his covers and laying to stare at the ceiling. 

It wasn’t too early that Cas felt the need to fall back asleep but it wasn’t too late that Cas thought he actually needed to get up and start the day. 

He looked over to his right to see Dean across the room sprawled out asleep on his back. The other man tended to always be hot so his blankets were kicked around his ankles and he was only sporting his batman boxers. Usually the sight of Dean in nothing but his boxers didn’t faze Cas since he’d been seeing it for almost four years but now, knowing what was underneath… it sent a thrill down his spine. 

He couldn’t resist. Slowly getting up from his bed, Cas stripped from his pajamas down to his boxers and made his way across the room to Dean’s bed and crawled up onto the end of it. He stared down at his still asleep best friend, waiting for the other man to start to rouse. 

He wasn’t used to feeling want so heavy that early in the morning but with Dean laying there looking so beautiful, Cas knew his body was only reacting to what it craved. 

They hadn’t talked much about things they’d like to try and Cas wasn’t sure if Dean was even interested in waking up to a blowjob, though the thought was on Cas’s mind, and he’d bet all his tuition on the fact that Dean would like it, he still wasn’t sure. Not wanting to do something Dean didn’t want, he shook Dean’s leg, earning only a slight snuffle from his friend. 

“Dean,” he whispered a few times to no response. 

Nudging his friend’s hip started to rouse the other man but he was still groggy. 

“Dean?” 

“Mm?” 

“Are you awake?” 

“No,” his friend groaned, throwing an arm over his eyes. Cas almost felt guilty about waking him up but the persistent need in his groin overshadowed it. 

“Dean?” He asked again, not wanting to let his friend fall back asleep. 

Dean didn’t necessarily seem grumpy but it was clear he wasn’t thrilled by it. “What?” he asked sounding vaguely annoyed. 

Cas was usually the grumpy morning person so this side of Dean was kind of cute. If only he didn’t have the miles of perfect skin before him, distracting him. 

“Do you want me to give you a blow job?” He asked, his voice still mostly a whisper. 

“Hmm?” 

Dean was clearly still groggy since his eyes couldn’t open completely.

If his friend really wanted to keep sleeping in, Cas wouldn’t mind. He was horny after all and could easily take care of it himself but with Dean there, he figured why not ask? 

“I can give you a blow job if you want?” 

His words must have penetrated Dean’s foggy brain because, despite the struggle, Dean’s eyes sleepily focused on Cas as he asked, “For real?” 

“Yes.” 

“Sounds like the best frickin’ wakeup call ever.” 

Cas laughed under his breath before lowering himself onto his belly between Dean’s legs. The bed wasn’t quite long enough for this to be perfectly comfortable but with a few shuffles they were able to make it work. 

Dean’s breathing was still steady and slow and his eyes dropped a little as he looked at Cas. Just that look alone gave Cas butterflies. How was it that each and every time he got to fool around with his friend, he felt overwhelmingly like the luckiest person in the world? How could seeing Dean half-awake in his boxers on his unmade bed make Cas want so deeply? 

It wasn’t fair how perfect Dean was at all times but it did thrill Cas to know he was the one who got to have him, at least for now. 

Not wanting to dwell too long in his thoughts he got to work on the task at hand. Just because he could, he ran his palms up Dean’s thighs, marveling at the muscle that Dean tended to keep hidden in loose jeans. His hands found their way to the thatch of hair at Dean pelvis and he scooted forward just a little more to get his face closer to where he was needed. 

He couldn’t help himself, he breathed in, tantalized by the scent of his friend that he’d grown so accustomed to. That’s when he got started, wrapping his right hand around Dean’s member in his boxers while his left arm slid up to keep Dean from squirming too much from the sensations. 

Dean had been doing a great job at giving Cas suggestions on what he could do with future partners. He always said Cas never needed to try it on him, but Cas found himself wanting to. 

With Dean, he wanted to try everything. 

Which is why after slipping Dean’s boxers off his legs, Cas had his tongue swirling all around the base of Dean’s cock before sucking each of his friend’s balls into his mouth. He gave them the attention Dean had admitted to liking, through a crimson blush, before Cas sucked the head of Dean’s dick into his mouth. 

Wanting more than anything to make Dean feel incredible he opened his mouth wider and took in all that he could and just let himself enjoy giving Dean this sensation. 

Eventually fingers found their way into Cas’s hair and pulled just the right amount, making Cas moan around the cock in his mouth. Not long after that he felt Dean’s hips start shallowly thrusting. It made him burn with desire but he pulled away suddenly, a fantasy flashing through his mind. 

“Mmm, no. Why’d you stop?” Dean asked, voice deep and gravely. 

“Get up?” 

Dean looked at Cas a little oddly before complying at sitting up. 

“Why?” He asked as Cas tried to crawl up to where Dean had just been laying. 

“Just move over. Trust me.” 

Confused, Dean shifted over until his back was flush against the wall and there was space for Cas to lie down. Immediately Cas did, settling back into the pillows and looking over at Dean. 

“I want to try it like this.” 

He might’ve been fooling around regularly with his friend but that didn’t mean he wasn’t still watching porn or thinking of things he wanted to try with Dean that he’d seen in said porn. 

“What do you mean?” Dean asked. 

“I want to suck you like this.” 

“Uh—what?” 

With a fond eye roll Cas tapped Dean’s hip. “Crawl over me.” 

He waited for Dean to get with the program and shuffle up onto his knees until this pelvis was yet again in Cas’s face. 

“You won’t be able to move though.” Dean commented, looking at the way Cas’s shoulders were nearly pinned down from the position. 

“Yes I will.” 

“How—how will I know if you don’t like it?” 

There was legitimate concern in Dean’s eyes and Cas was touched by it, but he was more concerned with the immediate need to get back to the good stuff so he wrapped his left arm around Dean’s thigh and demonstrated how he’d signal if he were uncomfortable. “I’ll push you off me. Come on.” 

“Oh. Fuck. Okay.” 

Maybe this was just as hot to Dean as it was to Cas because as soon as Dean’s cock was back in his mouth, Cas could practically see Dean’s eyes rolling into the back of his head. But what really got him was the way Dean moaned so dirty that Cas felt it all the way to his toes. 

He couldn’t take Dean as deep as he could in another position but there was something so inexplicably thrilling to be trying something like this. He knew it wasn’t anything special and he was probably doing it wrong but it felt like something exciting and a little naughty even though for Dean it probably would never crack top ten in his best sexual experiences. 

Probably trying to keep encouraging Cas, as he’d seemed to be doing more, Dean seemed to grit out, “Jesus, this is hot.” 

He hummed his agreement around the solid piece in his mouth and hallowed his cheeks just a little further, his neck a little uncomfortable at the angle but not terribly. 

Dean’s voice was rising in pitch, “Fuck. Are you touching yourself?” 

Castiel hadn’t even thought about it until that very moment, his hands too interested in grabbing Dean’s ass, just because he could. Now though he realized just how hard and aching he was. He maneuvered one hand away from the globe of Dean’s cheek it was settled on and began raking his hand over his own dick feeling just how pent up he’d actually become. His hips were squirming on their own accord, searching for more friction, so Cas doubled his efforts with his hand. 

He loved this. He loved the way Dean felt pressing in between his lips, sometimes a little unsteadily as his hips jerked and twitched. 

“Shitshitshitshitshit.” Dean breathed in a rush. It was the erratic movements above him that had Castiel gearing up to swallow around his best friend but that moment never came. Quickly, right before he was about to shoot, Dean pulled back, letting his release fall over Cas’s lips and chin. 

He felt Dean crawl off of him but kept his eyes closed as he continued trying to bring himself to the brink too. He was extremely aroused and with Dean’s come on his face Cas was certain he would follow any moment. He wasn’t quite there yet but he didn’t let up on the movement of his wrist, only stuttering a little when he felt warm puffs of breath in his ear. 

“Come on, you’re so close. That’s it.” 

Dean had moved to lay next to him, the solid line of his body pressing into Cas’s side. 

“Dean—“ 

“Keep going, don’t stop.” 

Cas could feel Dean’s forehead against his temple as his friend whispered hotly in his ear. 

He knew his moans were pathetic, and he felt like he was right on the brink but his body just wasn’t letting him go. He wanted so badly to be touched. So badly to feel the warmth of Dean’s skin against his own but knew the nose pressing against his cheekbone was the best he could get. 

“You’re so close,” Dean spoke again and Cas could feel his rich voice down to the base of his spine. How could his friend affect him so much yet Cas still struggled to achieve his orgasm?

“I can’t…” he whined frustrated, wanting so badly to feel the satisfaction he knew was coming. 

“You can. Don’t stop,” Dean encouraged, even as Cas squirmed next to him like a madman. “So fuckin’ hot. Come on.” 

Cas whined a little, trying so hard to get himself all the way there. His toes were curling and he felt like he was going to lose his mind. He wanted it so badly. 

Then it happened… a tentative touch to the flesh of his belly. Dean’s palm smoothed over him, and that did it. In an instant he was flying through his orgasm. Dean’s words were still whispering in his ear when Cas came back to himself. “There you go. So fuckin’ good.” 

His breathing still came in pants and his thighs still twitched with the slowing movements of his hands until eventually Cas allowed his body to just relax into the bed. 

“Don’t move. I’ll clean you up.” Dean declared before extracting himself from the bed. In a matter of minutes Castiel felt a washcloth being traced over the wet spots on his stomach and over his face to get any come off of him, his eyes still remaining closed. Even as Dean crawled back into the bed Cas couldn’t find the energy to be anything more than blissful. 

“Come here.” He heard whispered at his side, and that’s when he finally let his eyes drift open, to see Dean shifting on the bed enough to pull Cas into a cuddle. 

Castiel went willingly, resting his head on Dean chest and slinging his arm across his friend’s waist. He even felt bold enough to shift one of his legs over Dean’s, sinking into the other man’s embrace. It was indulgent and selfish but he relished in the moment, because Dean didn’t push him away and damnit it felt good. It felt right. 

“You’re seriously fulfilling a bunch of fantasies I didn’t even know I had.” 

Cas laughed against Dean’s chest. “I’m taking it that you enjoyed yourself?” 

“Dude, is that even a question?” 

“I’m glad.” 

“Yeah, same.” 

There was silence for a little while as they comfortably laid there. Cas could have fallen back asleep but his mind was filled with thoughts on just how perfect it felt to lay in Dean’s arms, he didn’t want the privilege to be taken away just by falling asleep. But what if he did fall asleep? Would Dean care so much? What if they both wore themselves out so much that they couldn’t help but pass out, wrapped up in each other? What if they fell asleep together after more intense sex… perhaps after intercourse? 

Cas tried not to tremble at the thought but images of Dean’s body atop his, crushing him into the mattress after an intense orgasm. He wanted that feeling so bad. Enough to feel just slightly brave enough to broach the subject. He pulled back a little, satisfied when Dean’s arm didn’t leave its place on the small of his back. 

“Can I ask you something?” 

“Sure?” 

Despite his claim of bravery, Cas’s voice still shook a little. He couldn’t meet Dean’s eyes so he occupied himself with tracing a few freckles on Dean’s collarbone with the tip of his finger. 

“I know I said… I know I said I just wanted to learn how to give hand jobs and blow jobs but…” 

“But what?” 

“What if… what if I wanted to learn how to do other things?” 

“Like what?” 

He looked up to meet his friend’s eyes and was comforted to see Dean’s face only show with patience and friendship, nothing in his eyes giving way that he suspected what Cas was about to say. 

It took him a moment to collect his courage but he finally managed to whisper out, “Like… what if I wanted to try having intercourse?” 

That’s when Dean’s face closed off. 

“Cas…” 

Heart thumping, Cas pulled away from Dean’s arms and tugged the blanket from the end of the bed around himself. He felt vulnerable but he tried to act strong, wanting Dean to understand his side of things before his friend could outright reject him. 

Dean must have sensed the shift in the conversation and pulled himself into an upright position still looking at Cas with a slightly terrified expression. 

“Dean look, I know this is probably so weird for you, but there is no one else I’d want to ask this of.” 

It was true. The thought of having intercourse with anyone besides Dean never really crossed his mind, not really. If he did imagine it, it was to some nameless, faceless blob and more in the sense of _‘what would it even be like?’_ But when he thought of it practically and imagined how he’d ever want it to be if he could have real sex with someone, it had always been Dean he wanted to experience it with. Even before all of this. 

Dean however, didn’t know that. 

“That’s because you haven’t tried to use your new skills to try and meet anyone else,” he challenged but it made Cas a little frustrated. 

“Dean! You said it yourself, you prefer a partner who is more experienced.” 

“And now you’re experienced!” Dean declared. “Anyone would be willing to do you.” 

“But what happens after we fool around like this and then they want to have sex with me? What happens when I don’t know what it will feel like or—or how much it might hurt? Or what if I don’t know how to keep them satisfied because I’m new to it all and don’t know any positions besides missionary? What happens then?” 

There must have been something wild and desperate in his voice because Dean’s tense shoulders deflated and he looked too understanding for Cas’s liking.

“Cas, you just need to meet the right person. They won’t care if you’re new to all of this. Look at how fun it’s been exploring the things we have? Imagine doing that with someone you’re really with. There’s nothing to be scared of if you meet someone you really like and wait to be sexual with them.” 

“I don’t want to wait, Dean. I want to experience this side of myself. I want to have fun. I want to not be worried that someone is going to be dissatisfied with my performance when we are together. Isn’t it more logical to do this with someone I trust, my best friend, so I can know what I’m doing wrong and not be embarrassed when I’m with someone else?” 

“Cas, you should want to be with someone you care about, especially for your first time.” 

“It would be with someone I care about; it’d be with you.” 

Dean looked a bit taken back by those words and even Cas wondered if the words revealed too much. 

“That’s different,” Dean croaked. 

“You care about me too, don’t you? You’re my best friend and we work well together. What’s wrong with trying a little more when we’ve come this far?” 

“Cas—“ 

He felt like he was internally panicking and couldn’t help but cringe at the pitch his voice had suddenly taken. But what was he doing? Dean was clearly uninterested and Cas couldn’t beg him to do this out of pity. No meant no. 

Who cared that he wanted to have this experience with Dean? It wasn’t like if they did have intercourse that Cas would somehow magically get to keep doing it with Dean forever. Eventually their arrangement would end and Cas would have to find other partners to do it with. 

It sucked because he was comfortable with Dean and wanted this with him badly, but it was stupid of him to think he could have this. Maybe he should go try and find someone else?

“No, I’m sorry,” he said, cutting Dean off from what he was going to say. “I shouldn’t push. You’re right. I can’t ask that of you. Maybe I should try and find someone else.” He didn’t like the way those words felt coming out of his mouth but what more could he do? “Would you be able to help me with finding someone?” 

There was an intense silence as Dean just looked Cas over, almost trying to read into Cas’s mind and figure him out. Cas felt his heart beating a tattoo into his ribs, wondering what the hell Dean was going to say. His friend seemed off but Cas couldn’t tell why. Dean didn’t seem mad but he certainly didn’t seem happy. 

“I’m sorry,” Cas added, knowing he’d probably messed up more than he realized, especially if Dean didn’t even want to help him find another partner someday. He moved to get off the bed but Dean’s words stopped him. 

“We can try to do… more.” 

“What?” 

Cas couldn’t believe his ears. Was Dean really agreeing to— 

“But I’m not having sex with you,” Dean cut in to his thoughts. “We aren’t going to cross that line.” 

He was stuck in a mixture between relieved and disappointed and didn’t know what he was supposed to say. He’d asked if they could start having intercourse and Dean was saying no but he was telling him they could do more? What more could they do if they didn’t go all the way? 

“Then how?” 

It looked like even Dean wasn’t certain but then his friend was saying, “Toys—we’ll start experimenting with toys or something. It will be almost like the same thing.” 

“But—“

“That’s my offer.” 

Cas let out a huff of frustration. He’d known Dean would try and talk him out of their arrangement going further. He’d known that Dean was only doing it to look out for him and ensure that Cas didn’t regret his choice but Castiel couldn’t help but feel a bit… rejected. Did Dean just not want to go further with him? 

Obviously. What the hell was Cas thinking? He was a guy. No way was Dean sexually attracted to him. He probably thought Cas was pathetic, practically begging for Dean to fuck him. He was such an idiot. Why would he ever think that Dean would ever want to have sex with him? 

Dean had signed up for blowjobs, nothing more. At least he was giving Cas a little mercy and letting them explore just a little bit more… whatever the hell that meant. 

It had to be good enough for now. 

“Okay.” Cas agreed, trying to plaster on a convincing smile.

**Notes for the Chapter:**

> Hi!! Do you like Dad!Dean? Angst and fluff? Heartbreak and tears? Happy endings? My DCBB titled Highway 20 Ride posted and I'd love if you'd read it if you haven't already. It's a very emotional one but I am very proud of it and put a lot of my heart into it. [Read it here!](https://archiveofourown.org/works/21317785/chapters/50767201)


	6. October 19, 2017

“Why are people bothering to even go back home for break? I mean can it even be called break? How can the school count the _weekend_ as part of the break? It’s a three-day weekend, not a break.” 

Dean looked out the window scornfully at all the kids with duffels over their shoulder, piling into cars and driving off to wherever the hell they went over break. For all his ranting and raving he was a little jealous of their ability to just return back home whenever they wanted. 

He knew Bobby and Jody were doing okay money-wise but he couldn’t bring himself to ask for a plane ticket no matter how bad he was missing them. They always told him that he could come home any time but he also knew they had Sammy they were still looking after. With his brother in the midst of applying for colleges and scholarships and eventually needing a reliable car to get him around whatever town he was going to go to for school, Dean just couldn’t let himself take any money that should be going to Sammy. Plus, it’d become a thing that he and Cas would sit out the shorter holidays and wait until the longer ones to go back home. Cas’s dad lived in L.A. and Dean’s family was in Sioux Falls and even though the drive from Las Vegas to L.A. wasn’t a bad one and Cas could even fly there for fairly cheap, he seemed to be willing to hang out with Dean’s sorry ass. 

“Veteran’s day is in a few weeks and we have Thanksgiving break a few weeks after that,” Cas responded easily, unbothered by the traveling students outside. 

“Hooray, a four-day weekend this time,” Dean exclaimed sarcastically, waving his hands in the air in mock excitement. When he already had Fridays off and therefore had three-day weekends every week, an extra Thursday didn’t really do much for him. 

“Five if you have a professor who has a flight to catch that Wednesday,” Cas added nonchalantly. 

“At least we don’t have classes,” Dean declared, finally pulling himself away from the window. “So what’s our game plan this time?” 

Cas had somehow managed to take over most of the futon so Dean playfully shoved his friend’s feet out of the way as he planted himself on the seat. The TV was on and Cas was entranced as he flipped through the options to stream. 

“Can we watch The Handmaid’s Tale?” Cas asked suddenly, the poster for the series up on the screen. 

“Seriously?” Dean exclaimed. It wasn’t exactly in Dean’s top five of ways he wanted to spend the weekend alone with Cas. 

“Hannah recommended it. She said it’s really good.” 

Dean stared at his friend for a little waiting to see if Cas was joking or not but the open and waiting expression on Cas’s face had Dean rolling his eyes and agreeing to Cas’s wishes. 

“Kay, fine. But then we watch all Star Wars.” 

Cas shrugged, “Obviously, that’s expected.” 

“Even the new ones.” 

“Dean that’ll take three days!” Cas protested, looking a little put out at the prospect. “How can we watch the show and all the movies?” 

Dean really was just fucking with Cas, he knew his friend didn’t love Star Wars to the same degree Dean did, plus Dean didn’t actually mind binge watching another TV series with his best friend but he rolled with the joke anyway. “Who needs sleep?” 

Cas still seemed unsure of Dean was joking or not but slumming it around the dorm for three days seemed to be an okay idea for him since he bargained, “You’re making the popcorn _and_ buying the candy.” 

“Puts you on beer duty,” Dean said with a grin. 

Cas slumped further into the futon and huffed, “Fine.” 

Dean would never admit how endearing he found grumpy Cas to be but damnit the guy was like a sulking cat when he didn’t get his way. Dean could just tell him he was fucking with him but where was the fun in that? 

He patted Cas’s leg and asked, “What do you want for dinner, grump?” 

His friend thought about it for far too long before stretching and yawning. It was unfair how sweet he looked as he turned to Dean and asked, “Can you make burgers?” 

Looking at that face, Dean wanted to say yes and give Cas anything and everything he wanted but he knew better. 

“I’m not going in the kitchen.” 

“Come on, it’s break. No one will be cooking in there,” Cas protested, nearly pouting. Dean had to laugh at his friend because that guy loved burgers more than anyone Dean had ever known but cooking in their dorm kitchen? 

“Hard no. Last time I was in there I ended up giving half my food away and you had to eat cold lasagna.”

He thought Cas would laugh at the memory too but instead the other man’s face fell a little as he turned back to the TV where the show was waiting to be played. 

“Fine,” Cas huffed, sounding very clearly not fine. 

Something was up, and had been for a few days and Dean knew it was his fault. 

Ever since they’d talked about going all the way or not, Dean noticed that Cas seemed pretty bummed. He wasn’t an idiot so he knew he made Cas feel rejected, he just didn’t know how to tell his friend that he wasn’t rejecting _him._

He knew it was supposed to be the “smarter” choice, saying no to having sex with Cas, but he wasn’t going to lie to himself and say he was happy with having to say it. What would have actually been the smartest choice would have been ending it altogether, telling Cas that he really was going to be okay going out and finding someone else but the thought—

It still twisted in his gut as he played back Cas asking him for help finding someone. Why did it make him want to break something even just thinking about Cas getting help from someone else? 

He was an idiot, a selfish idiot, who couldn’t stand the thought of not getting to do anything with Cas anymore. He wanted to tell Cas that he’d have sex with him in a heartbeat if he knew for sure it wouldn’t blow up in their faces but he was trying to be better than that. 

He still hated seeing Cas look so bummed. 

“I’ll order sushi for you?” He ended up asking, though he was ready to go out and buy everything to make burgers if that was really what Cas wanted. He’d even brave the damn communal kitchen and the dozen or so students who would undoubtedly try and mooch some of the food. Luckily Cas’s face lit up at the sound of sushi. 

“Spicy tuna rolls?” 

“You got it.” Dean got off the couch to grab his phone that was plugged in on his bed. As he was finding the number for the restaurant they liked best, Cas got up and crossed the room to go to the restroom. He patted Dean on the arm as he walked by. 

“Thank you, Dean.” 

“No problem.” 

He resisted the urge to reach out and pull Cas towards him and wrap him up in a hug. It’s not that they never hugged but not in the way Dean wanted. He wanted to stand there and keep Cas close, maybe breath in the scent of his friend in the way he always tried to hide when they cuddled. A simple ‘bro-hug’ wasn’t going to do it. 

This whole situation was starting to mess with his mind a little bit. One minute all he wanted to do was hold Cas and touch him and just be with him and the next minute he couldn’t stop thinking about getting his friend naked and doing any and all things possible with him. And now he had the new struggle of figuring out how to make Cas satisfied with going further without actually having sex. 

It was a sham and Dean knew it, he just wondered if Cas knew it too. What could Dean do for Cas with toys that Cas couldn’t do for himself? 

He wasn’t sure if he was ready to give Cas a blowjob or even jerk him off, but he figured since Cas hadn’t asked, that maybe it was something the other guy wasn’t interested from him? If Cas ever did bring it up, Dean would give it a try, not that he thought he’d be good at it or even like doing it, but he’d at least try. It just didn’t seem like Cas’s mind was even there? 

But he’d promised his friend they’d do more, so Dean still had to figure out what more meant. Cas seemed to really want to go all the way and Dean knew that meant they’d be finding out what felt nice when it went—

He didn’t want to mess this up and he didn’t want to make it suck either. Cas deserved something good, really good, and it was a shame all he had was Dean around to help him. 

He knew the smart thing to do right now would be to have a good long chat and maybe set some more boundaries and rules for what they were about to try but Dean was pretty sure everything would work out. He’d just keep following Cas’s lead.

**Notes for the Chapter:**

> These boys and their lack of communication skills will be the death of me! I hope everyone ends up liking where this goes, bad decisions and impulsive choices and all.


	7. October 21, 2017

This was new territory for them and Cas was a little out of his element. He was starting to learn that the hardest part about entering the world of sexuality was actually asking for what he wanted. He knew Dean was open to trying things out with him but the words still stayed at the tip of his tongue, especially since he and Dean had talked about doing more. 

He knew eventually he’d need to build up the courage to ask but a huge part of him was just hoping Dean would take the lead. It was his own insecurities making him think that if Dean was the one to bring it up again, then maybe he wouldn’t lose interest as quickly. Castiel hated thinking about it but he feared that if he was the one receiving the pleasure, even if from some toys, Dean wouldn’t care to do this with him anymore. Cas had _promised_ Dean that he wouldn’t have to do anything, that this arrangement would be solely based on Cas giving the pleasure… he didn’t want Dean to hate him for changing the dynamic. 

Castiel knew he was fully capable of using toys on himself. He knew he didn’t need Dean to assist him with using them but…. He felt a thrill every time he thought about Dean using them on him. About Dean maybe touching him more than just on his thighs or his chest like Dean’s hands sometimes fell. 

What would it feel like to have Dean’s fingers in him, opening him up so that he became loose enough to take a dildo? What would it feel like if Dean’s hands wandered a little too much and his knuckles brushed against Cas’s shaft, even if just accidently? What would it feel like to have Dean pressed up against him, pushing a toy in and out of Cas’s channel? Despite basically being constantly horny, he knew he wasn’t able to outright ask for any of that, but he did know how to entice his friend into at least being naked with him. 

He showered quickly and thoroughly as he’d taken to recently (just in case), forgoing his shirt but settling into his lounge pants. Maybe it was the growing need inside of him but he marched with a purpose over to the couch and plopped down beside Dean. 

“Take them off?” he requested, tugging at the edge of Dean’s pants which quickly vanished right after. 

Instead of moving to the floor, Cas shifted to lie on his stomach across the unoccupied space of the couch and had Dean’s dick bobbing in and out of his mouth in no time. He wasn’t sure if he was getting any better at this but he did know he was having more and more fun each time he did. That had to mean he was pretty okay, right? It’s just that he really liked hearing how Dean sounded when something felt nice, and he wanted to do anything he could to keep hearing that. He figured that’s why people did this in the first place. 

He always assumed that it would be a dull task to take someone in his mouth and spend who knows how long trying to get them off. He’d assumed that there’d be no satisfaction for himself but if he cared enough about the person he was with he’d endure it anyway. But that’s not at all how it felt at all. It _thrilled_ him to not be bad at this. It made his mind a little hazy every time he discovered new ways to take Dean’s length and be rewarded with a moan. And the way Dean would mutter encouragement and practically vibrate from his moans and groans… it was dizzying. 

With Cas on his belly against the couch, sucking Dean, the other man’s arm was left to rest steadily on his back. There was something so gentle about how Dean would rub Cas’s back like he didn’t know what to do with his hand most of the time but every so often he’d trail it up to Cas’s hair and tug a little, eliciting a small whine from Cas’s throat, making them both laugh a little. 

After a little bit of time, instead of Dean’s hand just resting on his back it started trailing up and down Cas’s naked spine, a sensation that felt too good to be real. Dean’s hands were warm and broad and left goosebumps on Cas’s skin as he trailed them up and down. Cas’s attention was too preoccupied with making Dean feel good that he didn’t notice as Dean’s movements grew bolder and his fingers started inching closer and closer to the waistband of Cas’s pants. 

Two… three… four times Dean’s fingers dipped just under the waistband before retreating away, back up Cas’s spine into his hair. He wasn’t sure if Dean was actually considering touching Cas’s ass and didn’t want to pressure Dean into touching him anywhere he didn’t want to, but Cas still craved it all the same. 

He felt a little sloppier as his mind was now swirling with fantasies of Dean touching him there, so when Dean’s fingers slipped under the band of his pants and made their way towards his crack, Cas had to pull off to let out a whimper. He panted as he allowed himself to just feel Dean’s fingers making their way to where he’d been dying to be touched. Right when he thought Dean was finally going to do it, the fingers moved to the side, gripping the roundness of one of his ass cheeks instead. 

Cas’s forehead dropped to Dean’s hipbone. 

“Don’t stop,” he heard Dean breathe from above him. 

Looking up, Cas wound up entranced by lust filled eyes. “I’ll keep going if you want but I want you to keep… uhm, keep doing what you were doing too,” Dean explained. 

Dean’s palm was still flush against his ass and Cas could only imagine how it’d feel if Dean kept exploring with that hand. _Needing_ Dean to touch him in a way he’d never been touched before, Cas nodded and brought his mouth back down to engulf Dean’s cock more enthusiastic than ever. 

As promised, Dean’s fingers started their decent back down the hills of his ass, trailing every which way but not _quite_ reaching the proper destination. 

He couldn’t have been more needy if he tried, Cas thought, as he canted his hips back, trying to press into the touch that kept evading his desires. 

He didn’t have time to worry if Dean was second guessing himself because before he knew it, the pad of Dean’s finger trailed lightly over his hole, making Cas keen from the feel of it. 

He’d touched himself there before, a few times, most recently in the shower but feeling someone else’s touch, _Dean’s_ touch there was completely different. It was unpredictable and more hesitant than any way he’d touched himself before but Cas figured Dean was still deciding if he was okay with it. Eventually Dean’s fingers stopped merely trailing over Cas’s hole, before finally starting to circle around it, pressing against the rim with a gentle pressure. 

Cas’s own cock was rock hard now. He was in no way ashamed of now rutting against the couch, wantonly moaning around the dick in his mouth. He doubled his efforts then, using his hand to massage Dean’s balls, while bobbing his head quickly, trying and failing to not think about the fact that Dean had his fingers against his rim. 

Unexpectedly, Dean’s hand pulled away from him and for a moment Castiel thought his friend had changed his mind, but before he could pull off of Dean’s cock, the hand was back, and those fingers now wetter than they had been. He suspected from Dean’s own spit. The pressure was back too, more intent than it had been before. Cas’s legs instinctively spread as he waited for what his body seemed to be burning for. He tried to stay focused on sucking Dean off but his mind couldn’t stop drifting to the feeling of Dean pressing against him. 

And then it was there, the feeling he’d been dying for; Dean’s finger pushing through the ring of muscle, oh so slowly. He couldn’t stop himself… he let out the most pathetic whine around Dean’s length and then suddenly Dean was coming down his throat and Cas was choking for the first time in weeks. Cas hadn’t even noticed how close Dean had been. 

Everything seemed to happen very quickly as he tried to get his coughing under control. With a few mumbled directions, Dean had Cas turn over onto his back and then Cas’s pants were off and Dean was sitting on the other side of the couch with his fingers circling Cas’s entrance. 

Cas could only stare at his friend who looked just as overwhelmed as Castiel felt. He thought about telling Dean that it was okay if he didn’t want to keep going—that he’d understand if Dean wanted Cas to finish himself off because his friend had already achieved orgasm, but Dean moved towards the ottoman, fumbling inside a little until he pulled out a travel size bottle of clear liquid. 

“I uh—I got this the other day—just… uh, just in case,” Dean explained, his cheeks tinged red from his orgasm. 

Cas didn’t really know what to say, so he nodded instead and waited as Dean clicked open the cap and poured some of the contents onto his fingers. Instinctively he let his knees drop a little further to the sides as Dean’s hand came back. 

It felt a lot more intense being able to stare up at Dean like this and watch his friend’s features as he brought his finger back to Cas’s entrance and pushed in. He _really_ liked having Dean touching him and that feeling just kept growing as Dean moved his finger in and out for a little before slowing to a stop. 

“Hey, touch yourself,” Dean commanded gently, voice sounding deeper than Cas had ever heard it before. Cas’s eyes flew opened, though he didn’t remember ever shutting them. He watched Dean staring down at where he was fingering Cas, and something about the look on his friend’s face made his own need feel ten times hotter. 

He didn’t rush himself as he wrapped his hands around his cock, just stroked it enough to keep his dick interested but not enough to distract him from the feel of Dean now pressing two slick fingers inside of him. But he wasn’t used to this feeling and he knew he was approaching his orgasm faster than he ever had before so when the slight burn of a third finger came, Cas knew he was done for. It took only four quick strokes before a silent scream ripped the air from his lungs and he was coming all over his chest and stomach. 

If fingers felt that good, he couldn’t imagine what it’d feel like to have all of Dean inside him but for now he’d take what he could get because—

“Holy fuck.” Dean spoke, completing what Cas was thinking. His friend’s fingers had just now stopped moving inside of him and slowly pulled out making Cas shiver. 

His arm flew over his face as he tried to catch his breath. He’d _never_ known something like that could feel so fucking good. He wanted a repeat of that performance pronto. His mind was complete mush. 

“You okay?” He heard Dean ask worriedly but Cas could barely even complete a nod. 

“Mhm,” he tried to ensure, a grin pushing at his cheeks. 

“Your brain a little fried?” 

“Mm.” 

Dean laughed a little. “Can you form real words?” Cas pulled his arm away from his face and finally looked over to Dean. The look Dean was giving him was a bit unreadable at the moment but Cas smiled softly at his green-eyed friend anyway. 

“Yeah.” 

“Was that—did you like that?” 

Cas couldn’t help but laugh and roll his eyes at the other boy. “Maybe a little.” 

“Good.” 

He hadn’t noticed that Dean’s hand was soothing up and down his thigh. The touch felt good, calming. He let himself be comforted by his friend’s hand just a little longer before he found his voice again. 

“Did uh—did you… were you okay with that?” 

“Yeah.” Dean answered instantaneously. Cas watched as his friend’s eyes roamed down his body before coming back up to lock with Cas’s. “It was different but… honestly? You’re—you’re uh… you’re like, really fucking tight.” 

“Sorry…” 

“For what?” Dean’s confusion was evident but Cas himself didn’t know why he felt like he needed to apologize. Was being too tight a bad thing? Did he like… did he squish Dean’s fingers? 

“I don’t know?” 

Dean’s look was still that of confusion but he shook it from his features a moment later and smiled down at Cas again. 

“I’m gonna clean you up. Stay here.” 

“M’kay.” 

Cas felt a little like he could take a four-hour nap and he didn’t want to fight it. He let Dean run a cool cloth over him and between his legs before he felt his friend nudging him over on the futon. 

“Okay, lazy, move over.” 

Once Cas was settled, Dean pulled him into his arms. It was admittedly a small fit on the futon and they probably should have laid the couch into a bed but Cas was not complaining about being pressed up close to his favorite person. Too foggy minded to really think straight Cas nuzzled his nose into the crook of Dean’s neck and found his eyes start feeling very heavy. 

If he happened to take a two-hour nap on his best friend’s chest… well that was nobody’s business but his own. 

For the record: right before he drifted off to sleep, his heart told him to be careful.


	8. October 22, 2017

**Notes for the Chapter:**

> The first part of this chapter touches on Dean's childhood abuse. Dean thinks about it casually and briefly mentions what was done to him but nothing is graphic. The few paragraphs after Bobby asks about Dean's classes are when it's mentioned if anyone would rather avoid it.

He was mostly staring at his computer screen wondering when the surge of motivation would hit him hard enough to finish the conclusion to his ‘History of The Beatles’ paper he was writing for one of his electives. Generally, he was pretty eager to hash out work for this course but his mind felt a little… off. No matter how much he tried to focus he kept coming back to the same thoughts and he was eager to ignore them just a little bit longer. Thankfully his buzzing phone called for his immediate attention. 

He picked up on the first buzz and felt his face light up when he heard his adoptive father’s voice on the other line. 

“Hey kid.” 

“Hey Pops,” Dean greeted back, already feeling ten times better just knowing Bobby was on the other end of the phone. 

“Haven’t heard from you in a little bit, you doing good? School okay?” 

Dean moved away from his desk and laptop and clambered onto his bed, settling in for a chat. 

“Yeah, I’m ready for break already though.” 

His dad harrumphed on the other end. “Classes getting harder?” 

He’d never admit it but he loved the concern he always heard in Bobby or Jody’s voices when they called him during the week or the way the sounded genuinely interested in listening to anything that bothered him. Really, he just loved remembering sometimes that he had people somewhere that missed him. 

Everything he had and everything he was, he owed to those two. Without a doubt, his life could have been so much different—and so much darker—if it weren’t for the two people he was lucky enough to call his parents. 

He vaguely remembers the shit his biological father put him through. He sometimes finds his mind flashing back to hazy memories of wrapping his baby brother in a blanket and holding him tightly at the bottom of the closest to sleep that night if his dad smelled funny again. He knows there was abuse. He knows that John hit him and yelled a lot and left a few circular shaped scars on the back of his left shoulder but his memory isn’t all there for most of it—something he’s both thankful for yet often frustrated about. 

He wishes he could remember the first few months with Jody but those memories are mostly lost to him as well, only vague flashes of moments, but most of what he knows is based on what his mom told him. When he asked her about it, years ago, she said he’d been timid and refused to let anyone hold Sam or feed him for nearly two whole months. She said that it even took Dean close to a year to really warm up to her and start accepting hugs. And it wasn’t until well over a year of living with Jody that Dean seemed accepting enough to be around Bobby more often. 

Dean does, however, remember how happy he’d been when Bobby did come to live with them. Bobby had set up the living room with Batman decorations and the two of them had a movie marathon watching all the cartoon Batman movies that Bobby could get his hands on. Dean even remembers that it was raining and Bobby let Dean go jump in the puddles with him. It was one of those nights that Dean assumed would be played on a reel if he ever made it to heaven or whatever. He remembers it as the first night that he thought that maybe _he_ got to have a good family like all the other kids at his school and on the TV too. 

Jody and Bobby ended up being the best thing to ever happen to him and Sam, and aside from a few dozen nightmares that still crept in, or a handful of childhood depression related issues, Dean had turned out pretty okay. He owed a lot to them and he didn’t know if he’d ever be able to show them just how grateful he was for everything they’d done. 

So, where some kids got annoyed with their parents calling all the time, Dean loved it and he’d humor his dad talking about school any day. 

“No, the classes aren’t getting harder but the professors are getting pettier. I mean I have this one who keeps giving us these damn essays with weird length requirements. The last essay had to be six and a half pages long and this one has to be eleven. Eleven, dad! It’s stupid.” 

The sound of Bobby laughing on the other end of the line was enough to make Dean crack up too. The old man sounded like he was smiling when he asked, “But you’re still doing okay in your classes overall?” 

If it weren’t for Bobby working with him when all Dean’s teachers tried to write off his lack of attention as ‘lashing out,’ Dean’s pretty sure he wouldn’t have made it through high school let alone gotten into college. 

Bobby stuck by him, no matter how much Dean had pushed back. He found ways to explain things to Dean’s racing mind and made learning not so grueling. Dean knew that even now, if something was too difficult for him, Bobby was just one phone call away and would stay on the phone with Dean for hours until it started making sense. 

“Yeah, I’m doing fine in them,” Dean confirmed. “I have a few friends in most of them so they’ll study with me and we work on a few papers together here and there.” 

“And how’s everything else? Car okay? You got enough money for gas and food?” 

“Yeah I’m all good there.” 

“Glad to hear it.” 

“Is everything good at home? Is Sammy good,” Dean asked, realizing just then, that it’d been a while since he’d called home. He suddenly felt like a jerk. He’d been missing his family so much yet had been too distracted with everything with Cas to even call. He hated not being able to drive home and see them whenever he wanted to. 

“Yup, he’s working on scholarship applications and there’s a few more schools he’s been looking into.” 

“His grades holding up?” 

“You know it.” Bobby said with a snort, as if Sam could ever get anything less than an A plus. “Anything new with you kid?” 

Like every time Bobby asked this over one of their phone calls, Dean had to forcefully shove any image of naked-Castiel from his mind. 

“Uh. Not really,” he answered lamely. 

“Any girlfriends I should know about?” Bobby teased, as usual. It was a dad thing, Dean knew, yet it made Dean stammer anyway. 

“Nah. No. No, I don’t have time for that.” 

He heard a low laugh on the receiver. “Oh really?” 

“Yeah. No girls. I’m not dating.” 

There was a pause on Bobby’s end, like he was waiting for Dean to say something more but eventually the silence ended, “Good. Keep it that way, idjit. Anyway, how’s Cas doing?” 

“Wh-what?” Dean nearly choked, feeling like Bobby somehow _knew_ but there was know way he’d know. He tried to keep his cool. “Oh Cas? Yeah, he’s good. Cas’s real good.” 

_Great job Winchester, real smooth,_ he thought, smacking himself in the head. Apparently, Bobby was oblivious since he kept on talking. 

“Jody’s been wondering if he’s going to come for winter break this year.” 

The momentary worry that Bobby somehow knew that he and Cas were having secret rendezvous in their dorm, immediately diminished hearing his dad ask that. He felt a little silly thinking that his parents would somehow just intuitively know that he and Cas were hooking up in secret, it made infinitely more sense that they’d want to know if his best friend was joining them for the holidays. But that left Dean wondering if Cas _was_ coming home with him. The previous year had been the first year Cas had come with him but their first two years they’d spent apart. 

Of course Dean wanted Cas to if his friend was interested. He loved having Cas around on breaks. The guy was his best friend and he missed him when they were apart but… with the shift in their dynamic? Would it be awkward if they were around Dean’s family? 

Would Sam, Bobby, and Jody figure out what they’d been up to? 

Shit… he’d need to talk to Cas about that.

“We haven’t talked about that yet actually,” Dean answered honestly. 

“Let him know he’s always welcome here.” 

“I will.” He smiled knowing that his family really did love Cas, but he couldn’t help but wonder if they’d still feel the same if they found out what he and Dean had been up to? 

He couldn’t see his family being against him being with a guy but what he and Cas were doing? This hooking up, no strings attached, friends with benefits type deal didn’t seem like something his parents would understand. He had a feeling they’d be disappointed in him for not treating Cas the way Cas should be treated. Hell, he was mad at himself for it too. 

Before he could spiral a little more into his thoughts, Bobby kept talking, “Oh. That reminds me. You need to call your brother. He still wants to come out and see you and Cas but he wants to do it when schools in session. He’s been bugging if we can send him out right before you go on winter break. Maybe even Thanksgiving break.” 

Dean perked up at the mention of his brother coming to visit. 

“Alright, I’ll call him now.” 

“Good. Miss ya’ you idjit.” 

“I miss you too.” 

He hung up with Bobby but wasted no time before he found his brother’s name in his contacts and pressed call. 

“Dean?” 

“Hey Sammy.” 

“What’s up?” 

“Dad said you might want to come out for a little?” 

“Oh! Yeah!” It was the genuine excitement in Sam’s voice that had Dean smiling over the phone. “I’m thinking about it. Him and mom said they’d be cool flying me out if I could stay with you. I don’t know when’s a good time for you though.” 

Out of habit, Dean peered over at the calendar on the opposite wall. “I have most Friday’s off but I don’t want you to miss any school. So probably on one of the breaks would be best.” 

“I kind of want to tour it when school’s in, though,” Sam’s voice had just enough disappointment in it to make Dean want to fold like a card table but the thought of having to still go to classes while his brother was visiting didn’t sound as much fun as getting to hang out with Sam as much as he could. 

“I don’t know if that’s really gonna work for me though, dude. I won’t really be able to give you any tours if I’m in class.” 

“Would Cas be able to?” 

“Maybe? He has mostly afternoon classes so he could probably take you in the morning.” 

“I’ll text you more and figure it out okay?” 

“Yeah!” Dean actually felt giddy at the thought of Sammy coming out and visiting him at UNLV. He knew logically the kid probably wouldn’t end up going to his school since he’d always seemed pretty set on living in California or any state with a beach, but Dean still wanted to have the chance to convince his brother to be a little closer to him. 

Damn, he missed having his brother around all the time. As much as they’d pick on each other and as much as Sam could be a snot-nosed brat at times, he was Dean’s closest friend growing up. 

“How’s everything back home?” Dean asked, not wanting to get off the phone just yet. 

“Same as normal. Nothing really special going on.” Sam shrugged off like a typical teenager. Dean could hear the video games through the receiver and knew his brother was only half listening to him. 

“Okay, well I’ll let you get back to your eventful life.” 

“I miss you.” 

A surge of emotion hit him and Dean tried not to let himself get misty eyed. “Miss you too, kid. Text me okay?” 

After hanging up the phone with his brother, Dean had a new sense of energy about him and managed to bang out his essay in record time. He even got a head start on some proofs he had for one of his engineering courses. Needless to say, he was in a good mood when Cas came walking in the door and dumped his bags. 

“Heya, Cas! Day okay?” 

“It was.” There was a smile in Cas’s voice. “You seem happy. I take it your day went well also?” 

“I called Sammy earlier and he said he wants to try and find a time to come out and see the campus.” 

Cas looked genuinely pleased by the news. “That’s exciting. It’s been a while.” 

“He wants either you or me to give him some tours around campus. I told him you’d probably be up for that.” 

Dean watched unabashedly as Cas stripped out of his school clothes and into a pair of pajama bottoms. He wasn’t sure if getting to watch his friend half naked was really a part of their deal but he really couldn’t help himself. Cas was… fuck, Cas was hot okay? It didn’t take anything more than a pair of eyes to see that even though Cas was still filling out and was more on the lanky side, that his lean muscle was getting a little bulkier every year and he was starting to get kinda… ripped. He was a hot guy. It wasn’t like Dean was the only one who noticed that fact about him. Other people had eyes too. 

His heart rate picked up a little watching the muscles of Cas’s back shift as he pulled up his pants and tied them off. Warmth started to fill his belly just thinking about getting Cas all the way out of his pajamas—why wear them around anymore anyway? It’d be so much easier if they both just came home and were naked all the time, right? 

“Of course I’ll take him,” Cas declared, pulling Dean’s mind out of the gutter that it’d been so perpetually stuck in lately he was probably about to find Pennywise. What was Cas doing to him? 

“I’ll let him know,” Dean said with an awkward cough, trying to casually readjust how he was sitting on the couch. 

“Sounds wonderful.” 

Cas plopped into his beanbag and wrapped his blanket around himself before flicking the TV on and getting the next episode of Dr. Sexy up. “So, what’s supposed to happen this week with Dr. Piccolo? Did she survive the bomb in that man’s rectum?” 

Dean tried to ignore the little sting of _’rejected’_ he felt when Cas didn’t choose to sit next to him on the couch, but… it wasn’t like he offered either. Besides, it wasn’t like they cuddled except for when they engaged in their “learning” and he sure as hell did not expect Cas to want to touch him every single day. So it was definitely normal for Cas to not sit next to him if he didn’t want to “learn” with Dean today. It was fine. Really. 

Fuck.

What was wrong with him? He was starting to act like such a melodramatic teenaged girl on all those TV shows. 

He was screwed.

* * *

**Friday October 27, 2017**

He’d just been three fingers deep in his best friend’s ass and now he was holding him against his chest like it was normal. 

And okay, maybe it was their normal but it was starting to make Dean wonder if there were any other friends out there who finger fucked their best friends after getting an extremely sloppy blowjob from said friend. 

Probably somewhere in the world, right? 

He just didn’t know how much longer Cas would want to do this with him before he started asking for more again and Dean honestly didn’t think his resolve was strong enough to withstand Cas asking for sex again. He knew just one look into those pleading blue eyes and Dean would probably crumble. He was barely keeping his resolve together by a tiny thread because when Cas asked him if they could have sex, Dean wanted more than anything to say yes. 

But now? Now that he’d felt how fucking velvety and warm Cas felt around his fingers he couldn’t help but wonder what it’d feel like to have Cas’s body underneath his—to have his cock inside that tight— 

He needed to stop letting his mind go there because he couldn’t do that. He was already crossing so many lines to begin with but he couldn’t do the most inherently wrong thing he could think of. He could not steal away Cas’s last bit of innocence just because his libido was raging all the time now, no matter how much he wanted to. 

He was the worst kind of asshole imaginable. But he’d never hurt Cas. He would not do that to his friend. 

But he could give Cas what he wanted in their own ways and he wanted to do as much as he could for Cas because seeing his friend come? It was like watching someone completely crumble into dust under his fingertips after dynamite went off inside of him. 

Dean didn’t think he was bad in bed, in fact he always thought he was pretty decent but… Dean had seen nothing like this from anyone. Yeah, maybe it was different because Cas was a dude and maybe dudes got off a little more explosively than girls did, but even Dean was coming harder than he ever had, even with the bendiest of chick’s he’d fooled around with. 

It was different with Cas and Dean didn’t know (or didn’t want to know) why. 

Still, he wanted Cas to feel amazing. He wanted to draw as much pleasure out of his friend as he could so that Cas would know how good sex and fooling around could feel. He wanted Cas to be confident in himself so if he ever were in relationships in the future, he’d have a frame of reference. Dean wanted Cas to know what to ask for to give himself the best feelings and the best time. 

Dean was still a little horny and apparently so was Cas because even though they were technically in the cuddling stage, Dean still had one of his fingers lazily pressing in and out of Cas’s loosened hole. He couldn’t help it, okay? He liked the little mewls that were escaping Cas’s lips. 

“Dean,“ Cas breathed hotly against his collar, making Dean smirk a little. He loved that he affected his friend this bad. 

“Yeah?” His question was innocent but the deep press of his finger was not

“I—oh!” 

“What do you need?” 

Cas’s leg that had been thrown over Dean’s own shifted just enough to align Cas’s dick against Dean’s hip. His friend seemed almost unaware of the fact that he was grinding into him and Dean didn’t care in the slightest. He just pressed another finger back into Cas’s ass, pumping with more of a purpose now. 

Cas breathed into his neck, mumbling incoherent words and making pitiful sounds that only increased the speed that Dean thrusted his fingers. His friend’s hips started moving with more of a purpose. 

Dean had gone insane. Each and every day he kept crossing more and more lines but fuck if he cared. Not when Cas’s dick was literally four inches away from his and the walls of Cas’s ass were fluttering around his fingers. “Oh fuck. That’s it. You’re gonna come again aren’t you?” 

“Hng—yeah. Oh! Dean.” 

Dean’s eyes rolled into the back of his head as he groaned. How the fuck was this so hot? He’d literally just gotten off fifteen minutes ago. 

“Wanna come with you.” He declared. 

And that’s when Cas got with the program, reaching down to tug on Dean’s cock as he continued thrusting against Dean’s hip. 

They were so close like this, so much skin was touching and it was making Dean lose his fucking mind. All he wanted at that moment was to pin Cas down and wrap his friend’s legs around him. He wanted to press into the tight warmth that was currently encircling his fingers. He wanted to fuck his friend hard and deep and watch as Cas fell apart beneath him. He wanted to hear Cas rasping his name and feel him clawing at his back. 

Holy fuck he wanted to fuck his best friend. 

He wanted it so bad. 

“Fuck, fuck, fuck, fuck, fuck.” Dean cursed as his second orgasm of the night hit him like a train. It wasn’t even a beat later that Cas followed behind him. 

“Dean, I—Dean. Ugnh!” Cas’s moans were muffled by the crease of Dean’s neck. 

It took a few moments for both of their spasming limbs to start to calm down. And even though no part of him wanted to stop touching Cas he finally pulled his fingers away, wiped them on the sheet, and started gently rubbing Cas’s back as he slowly stopped shaking. 

Dean couldn’t move. He definitely had Cas’s come on his hip and his own on his stomach and they were definitely chilled from their sweat damp bodies and the AC so they were probably not in the most comfortable position but his limbs felt like lead and Cas felt like dead weight at his side. 

“You okay?” 

“Mhm.” Cas mumbled into his neck. A moment later Dean felt his friend shiver at his side. 

“Cold?” 

“Little.” 

Dean kicked his feet, trying to get the sheets untangled from the bottom. Eventually he got enough up to tug at the thin twin sized material that hardly did anything to warm them up, but it was better than nothing for the time being. 

He thinks they dozed for maybe twenty minutes or so but eventually he knew both of them were awake yet neither of them were pulling away from one another. 

It scared him how comfortable this was. Shouldn’t it feel weird to have his best guy friend lying next to him naked? Shouldn’t it feel weird to feel a soft cock against his hip and the scruff on his friend’s jaw against his shoulder? Why did it feel like everything Dean couldn’t put words to? Why did this feel right? 

Dean could feel his heart and his mind going at it, full battle axes and armor and everything, lashing out against each other trying to prove that one was correct. Knowing the internal battle he was facing Dean still felt inclined to listen to his mind; Cas was his best friend, he was only here to help Cas out, there was no way anything would come out of this arrangement because all it was, was an arrangement. Cas was using him to get experience to use with other future partners. It was not to use with Dean in some kind of _relationship._

Dean was the one to help him because he was the most convenient. It wasn’t like Cas picked him because Dean was special or anything; it wasn’t like Cas had feelings for someone like Dean... No Cas could do way better. He _would_ do better than Dean once Dean stopped being selfish and decided to let Cas go out into the world to use his new skills. 

Dean’s heart just needed to learn to shut the fuck up and stop getting too overeager when it came to the blue-eyed sex God he had in his arms. 

But not yet…

“So I was thinking we should probably get you some toys soon? Start trying them out,” he asked, trying to sound casual. 

Cas shuffled a little before he sat up enough to look down at Dean. He seemed to be pondering the idea of getting some toys before he turned a slight shade of pink and turned away. Bashful almost. “I uh—I should probably order them online?” 

“I think it’s better if you go to the stores and test them out.” Dean shared, moving to sit up on the bed as well. “That way you can check the sizes and everything.” 

“Have you... been to a sex store?” 

“Uh. Once. This one girl I fooled around with was into toys.” Dean didn’t bother to say much else and Cas didn’t ask any questions. Instead, he continued looking mortified at the thought of actually stepping foot into an adult shop. 

“I don’t... I don’t think I’d be comfortable going in there by myself. Online is probably best. I’ll just—I’ll just order a few different things.” 

Fuck. Why was it so fucking cute to see Cas blushing like this? 

“We can go together.” Dean said quickly, trying to put Cas out of his misery. “Just not to one around here or anything.” He added, thinking about how awkward it would be to run into someone they knew as they were trying to buy dildos. Yeah, he’d definitely rather _not_ deal with that. 

Cas didn’t seem convinced though. “I’m sure online is just fine.” 

Dean rolled his eyes. He knew Cas was shy and would probably be a bit anxious going in but Dean also knew his friend would feel much more comfortable after he talked to a consultant and got something that would actually be good for him instead of based on what some online review said. 

“The consultants there know their stuff. You’ll find something right for you faster than online.” 

“Okay,” Cas agreed quietly, he looked uncomfortable but he must’ve known Dean wouldn’t just throw him to the sharks since he nodded and smiled slightly. “We can go. Is tomorrow okay?” 

“Works for me.” 

For a moment it looked like Cas was going to say something or maybe lean back in and lie down with Dean for a little while longer but his hand trailed through a glob of come still on his stomach and he grimaced. 

“I should go shower.” 

That same sting of rejection from a few days ago hit Dean again but he forced it away and gave his friend a winning grin. “Need a buddy? You know, I don’t want you to slip and fall or something.”

“You’re incorrigible.”

“You love it.” 

All that earned him was an eye roll.

* * *

**Saturday October 28, 2017**

As they had discussed, they drove a few miles away from the college to find a store they wouldn’t be recognized in. Being as they were in Las Vegas they really had a slew of places to pick from and decided to go with one that didn’t have garish objects in the window. He didn’t want Cas to have an aneurism from anxiety after all. (Okay, maybe Dean was a little intimidated by mannequins dressed in leather and feathers with floggers in their hands—sue him). 

This place felt clean and simple. There were of course some more obscure items that Dean didn’t think he’d ever find sexy but there weren’t dicks and strap-ons hanging from the ceiling so that was a plus. 

When they walked in a woman came over and asked if they had any questions and Cas had taken off with her, leaving Dean to peruse the store for the time being. He started wandering the small trinket area with the dick straws and magnets before he found himself wandering the aisles. He was blown away by the sheer amount of vibrators that were offered. Seriously, how was someone supposed to pick which level of vibration was ideal? And the different shapes and textures that went along with them? It was insane. 

Eventually he found himself drifting around the store aimlessly after a while and just staring at the different objects on display wondering how many people actually used them. Currently he was in an area for anal stimulation. That’s how one of the consultants cornered him. 

“Are you interested in any of these?” 

“Oh what?” Dean stammered for a second before he followed her gaze to the items on the shelf. “Am I? Oh—no. No. Just trying to figure them out.” 

“They’re prostate massagers.”

He felt himself blush as he tried to not be an awkward fuck talking about ass toys. “You just stick them in and then let it do its thing?” 

_Smooth, Winchester._

“Essentially.” The woman agreed. She had blue and green hair and a metal lip ring but looked far less terrifying than most people with wild colored hair who worked in sex stores. She looked normal, really. Even her attitude was kind as she explained the toy Dean was standing next to. “People like to masturbate while using them generally.” 

“Oh.” 

“Would you be interested in something like that?” 

“Oh. Oh no. I uh.” He felt like an idiot stammering like this but the thought of something that bulbous going into his—nope. No thanks. “I’m not into anything going—no. I was thinking for my friend?”

“Blue eyes?”

“Yeah, he’s uh, new to this and I wanted him to come here to get some things he could try out.”

“What a considerate partner… friend?”

“Uh—fr-friend.”

The woman accepted his answer for what is was, but even Dean knew he didn’t sound all that convincing. 

“Were you hoping for items you could use together or for his use?”

“His—his use. That maybe could be used on him by a p-partner.” 

The woman nodded her head and gestured to a device that was a bit longer than the other ones he’d been looking at but still stated it was a prostate massager. 

“I would recommend this massager as many of the reviews have reported hands-free orgasms from it. It’s also easier to find the prostate since it’s larger than many of the more targeted ones.” 

“Uh—okay.” 

“But if this isn’t something you’re looking for there are some dildos I can show you that might be good.” Dumbly he followed the woman around the corner and to the next aisle where she pointed to one of the smaller dildos. This one had a bit of a curve to it. 

“So this is my recommendation for beginners since it is a very pliable silicone and the length and width are not outrageous. Many costumers of varying experience levels and sexualities have recommended it.” 

“Okay. That, uh, that sounds—“ A few feet away down the aisle was his friend and Dean breathed a sudden sigh of relief. “Oh Cas, there you are, come here.” 

His friend smiled and showed off the store shopping bag that had a few items in it. “Dean! The lady has been showing me so many things. I had no idea that there were such specific items. Did you know they make anal plugs with tails on them?” 

“Ha-uh, no.” Dean blushed, rubbing at the back of his neck. “I did not know that. Uh, did you get one?”

“Oh no. Well not one with the tails but I thought getting a plug would be something worth trying. Have you found anything?” 

“Yeah she was—“ Dean looked around to see that the consultant had left them, “She was just here but she uh was telling me that this a good beginner uh, toy. I think you should go with this one.” 

He showed off the smaller dildo that definitely looked the safest choice to him. Especially when he glanced all the way towards the end to see one that looked about the size of his fucking head. How did anyone… nope! He wasn’t even going to finish that thought. 

Cas apparently was displeased with Dean’s choice as he assessed the object. “But it’s so... small.” 

“Dude, that’s pretty much the size most guys are.” 

“You’re significantly bigger than this though. Why would I want to get this one?” 

If Dean’s chest puffed out just a little at that remark, he hoped no one saw but… damn. Bless Cas and his smooth ego stroking abilities. Still, Dean trusted the woman and figured that if she recommended the smaller ones for beginners then it would be for the best, right? 

“It seems like a good beginner one though. And I’m telling you most guys will not be this big.” Dean said, gesturing to some more girthy ones. 

“But this one looks more like your size.” Cas’s eyes were focused on one that was actually more comparable to Dean’s own size, this one perhaps had an inch on him. 

“Cas, it’s kind of big to start with.” He argued anyway making Cas huff a little. 

“But if you’d have agreed to have sex with me I would have been ‘starting with’ a penis this size. It’s not like it’s not going to fit with adequate prepping.” 

Dean sucked in a breath realizing just how right Cas was. If Dean had agreed to it, he’d have had to get his dick into Cas’s tight hole somehow… and that thought suddenly made him very anxious. What if he’d have agreed and had hurt Cas? Which he would have because, holy fuck, Dean didn’t know what the hell he was doing. 

He was going to hurt Cas and he was going to make Cas hate having sex… what the fuck was Dean even thinking? How could he have agreed to do more with Cas without having any fucking clue what he needed to do to make sure that his best friend wouldn’t get hurt. Hell, he’d only randomly thought about grabbing lube last week because it suddenly dawned on him that his own ass didn’t get wet when he was turned on which meant that if he wanted to finger Cas it wouldn’t have gotten slicked up on his own like a girl does. 

Suddenly Dean felt overwhelmingly out of his element. 

“Cas...”

“I’d rather go with one more sizable and comparable to the penis I have experience with.” 

“I’d feel more comfortable going with the smaller one. It’s not going to be comfortable your first few times.” 

“Then we get both.” Cas said with a shrug, grabbing each box and putting them into his bag. “When the smaller one proves not to be as pleasurable, we’ll switch to the larger one.” 

“You’re a stubborn bastard. I’ll give you that.” Dean’s anxiety still felt palpable but he didn’t want to dampen Cas’s mood. His friend actually seemed excited to be here and experiment with the things they were buying. 

“Would you like to see what else I got?” Cas asked with a grin, looking like he’d just purchased a bucket of candy or something. 

Dean couldn’t stop himself from smiling. “Yeah, show me.”

* * *

** October 29, 2017**

Cas had bought a green silicone butt plug, blue anal beads, a vibrator, and the two dildos that they’d argued over. He’d been very interested in starting off with the anal beads and of course Dean couldn’t say no. So after washing it thoroughly they’d played around with them that night. Dean could tell they weren’t Cas’s favorite since neither of them really knew what to do with them, and even after pausing for a little to Google what to do, they were still clueless. Regardless, Cas had a good orgasm but Dean could tell that it wasn’t as toe-curling as he’d gotten use to watching. 

So when Cas had asked if they could try one of the dildos the next night, Dean readily agreed, wanting to redeem himself a little. 

Even though he didn’t care if he didn’t get off at all, and was solely focused on making sure that Cas came better than he did the night before, Cas seemed focused only on Dean’s own orgasms. Like the first time Dean had ever fingered Cas, his friend laid down on the sofa to suck Dean down so that Dean could get his fingers in him and every time he had Cas like this, Dean couldn’t help but feel like a virginal teenager again getting to touch someone for the first time.

He tried not to get embarrassed each time touching Cas’s ass made him shoot at ten times the rate as usual, but fuck… every fucking time. “It’s getting embarrassing how fast you can get me to blow. Like damn dude, are you trying to set a record?” 

“Maybe…” Cas grinned devilishly, suckling around Dean’s spent cock. 

“You’re making me feel like I’m thirteen again. Can’t even last five minutes.” 

“I like it.” 

Dean felt a jolt of _something_ course though him just looking down at Cas in that moment but he tried to tamper it down, not wanting to fuck with those types of emotions at the moment. He had a job to do, and that job involved getting a fake dick up his friend’s ass until his friend came as hard as possible. 

“So do you want to do this on your back or stomach?” He asked, watching with silent glee as a flush crawled up Cas’s neck. 

“Uh, stomach is fine.” 

Dean nodded in agreement and had Cas climb onto his bed and get a pillow under himself while Dean went to grab the toy from where they’d left it on Cas’s desk. 

When he crossed over to the bed Cas had a look on his face that gave Dean pause. 

“What’s wrong?” 

“I was just thinking…. I can—I can prep myself if you don’t want to… I can—I can just do it all myself… I—I shouldn’t have assumed…” 

“No!” Dean practically shouted. He back peddled quickly, not wanting Cas to think Dean was too eager. “I mean… it’s cool. It’s like—it’s like we’re pretending to have real sex. What it would be like, right? So you kind of need a partner for that right?” 

“Uh, yeah—yeah I guess so.” 

Dean could still sense some hesitance in Cas’s voice and he scrambled to convince Cas that this was a good idea. Fuck. Dean needed Cas to say yes to let Dean help him with this. He didn’t want their arrangement to end here, especially since Cas hadn’t even gotten off that well yesterday and Dean didn’t want Cas’s last memory of their time together being a shitty orgasm. 

“You do. And—and this way you can learn how to vocalize the things you want. Yeah, that’s actually really important to learn.” Dean was thankful that his slight desperation was actually kind of making sense. “You have to be open to communication with your partner because if they’re doing something you really don’t like and you just keep silent about it thinking it will get better… it will never get better. So you—you need to learn how to say what you want, you know? You won’t be able to learn that if you’re just doing this by yourself.” 

“Oh. That—that makes a lot of sense. Okay.” Cas agreed, he looked a little more comfortable. “You’re sure though?” He asked. 

“I want you to feel comfortable when you are with a real partner. I want it to be good for you. Only if you want to do this.” Dean was quick to add. He realized that maybe his panicked attempts to keep Cas weren’t fair, especially if Cas really didn’t want Dean’s help anymore. “If you don’t want my help though, I can just leave and let you do this yourself?” 

“I do! I still want your help.” Cas said suddenly. That’s when moved to roll over again but Dean stopped him before he could. 

“Wait. How about—how about you lay on your back? I want—uh most of the time first times are uh in the missionary positions so I uh, I want you to experience it that way but if you hate it you can lay on your stomach obviously. Or if that’s how you’d prefer it then it can be on your stomach I was just thinking…” 

“I’ll lay on my back.” Cas said calmly. Maybe he could tell that Dean was just as nervous as he was. He moved the pillow under his lower back and put a few under his head as well. “This okay?” 

“Perfe—yeah—yeah, you’re good. You’re good like that.” Dean stammered, looking down at his naked friend. He couldn’t get over how fucking perfect Cas looked. How much skin was there just for Dean to touch—no. He couldn’t let himself touch or else he’d probably never be able to stop. He had to remind himself he wasn’t helping Cas out for his own pleasure, it was for Cas. To make Cas feel happy and confident. That’s what mattered. 

“Uh, maybe, maybe bring your knees up?” Dean suggested. Cas complied immediately, bringing his legs up just enough that Dean could now see his hole. “Yeah, like that. Good.” 

Nervously excited, Dean crawled up to the end of the bed. His mouth went a little dry as he looked down at Cas laying there with alert, eager eyes. Dean didn’t exactly know what he was doing apart from some frantic googling when Cas was sleeping the other night but he figured as long as he took care of Cas he’d be fine. 

He reached over to where they’d dropped the lube on the bed and clicked it open. He drizzled a little onto his fingers and took some time to warm it up. There was something charged in the way Cas’s eyes refused to leave Dean’s as Dean moved further between his legs and rubbed the warmed lube around his hole. And Dean too couldn’t look away. He was drawn into the way that Cas’s lips parted as Dean’s first finger breached his rim and slowly began pressing in. A small whine escaped in a breath and Dean instantly soothed his hand up and down Cas’s thigh. 

“Is that okay?” 

“Mm? Oh—oh yeah. Yeah, it’s good.” 

He took his time. He didn’t care if it took him nearly ten minutes to work just two fingers into Cas… Dean needed this. He needed to touch his friend the only way he was allowed to for as long as he was allowed to. 

And Cas let him. 

He had no clue how long it had been until he was able to fit three of his fingers. 

“Do—do you feel stretched? Nothing hurts?” He asked softly, hardly a whisper. 

“I’m good.” 

“Okay I’m going—I’m going to uh—I’m going to use it now.” 

“Okay…” 

There were nerves in Cas’s voice but they verged more on eagerness than anxiousness. Dean took his time slipping his fingers out of Cas and lubing up the toy generously before lining it up with Cas’s fluttering pink hole. 

“Tell me if you’re okay.” 

And maybe because Dean was still trying to draw this out as much as possible, he didn’t press in right away. Instead he rubbed the silicone head around Cas’s perineum and traced it over his hole just to watch the way Cas squirmed and hear how he gasped. 

It was when Cas let out a whispered version of his name that Dean couldn’t deny him any longer. Gently he pressed the tip of the toy inside his friend and slowly rocked it in and out until Cas’s body accepted it fully. 

A sharp breath of, “oh,” was pressed from Cas’s lips. 

All of Dean’s movements stilled in that instant, assuming the worst. “Am I hurting you?” 

“No.” Cas breathed out. “No. It—it doesn’t hurt at all. Just—just feels… full?” 

Dean’s own breathing was heavy and his dick was definitely interested in this situation but he ignored his own needs and focused on the most important ones. 

“Are you ready? Can I move it?” 

“Yes. Please,” Cas panted. So Dean did what he needed to. He slid the toy nearly all the way out before pressing back in, doing his best to imitate what he would do if he were the one inside of his friend. “Oh whoa.” Cas said immediately. Dean continued with his movements and Cas continued with his stunned vocalizations. “Oh whoa… that’s… whoa.” 

“Good whoa or bad whoa?” Dean asked, still pressing the dildo in and out of his friend.

“Hngh—g—good whoa.” 

Cas’s hands seemed to tremble at his sides as he tried to clutch at the sheets. Soon enough his hands were wandering across his chest, splaying out and clutching like he was trying to get a grip of something clawing through his body. Into his hair they went and back down his chest, caressing down to his tummy and back up again. It looked like he was searching for something, trying to get hold of something to tether himself to the world. 

Dean couldn’t keep his eyes off him, even as he pressed the dildo in and out of Cas’s ass, he couldn’t keep his eyes on the way Cas’s eyes closed and his body writhed on the bed. Not able to think straight, Dean let his left hand wander up Cas’s thigh and up across his belly, suddenly meeting one of Cas’s stray hands and gripping onto him tightly. 

Cas held onto his hands with a vice grip. 

“Dean—“ 

“You okay? Is it too much?” 

“No—no. S’good. Can—can you go—can you try it faster?” 

Dean had to swallow a groan, as his mind surged with images of Cas whispering that into his ear as Dean fucked into him. “Yeah…” Dean whispered, immediately indulging in Cas’s wish and jerking his wrist faster. “Like this?” 

“Mmm—yeah—yeah that. Oh god.” 

“What do you need?” 

“I—I need—oh god.” 

Cas’s hips were wriggling on the bed and Dean could see the way his cock was practically begging to be touched. 

“Touch yourself. Come on.” 

Even though Cas wasn’t left-handed, his right hand was currently latched onto Dean’s. He brought his non-dominant hand around his shaft and started tugging with a purpose.

He was so worked up that Dean thought it’d only be a matter of seconds before his friend exploded. Yet, right when Dean thought Cas was at his peak his friend slowed down the movements of his hands. 

“Dean—Dean—Dean…. Wait.” 

“What?” 

“I—can I—I wanna try the bigger one.” 

“You’re so close though.” 

“Please—please I… I wanna feel.” 

There was no way Dean would deny Cas this with the way he sounded. But the way he looked? Dean was done for. Cas’s skin was flushed and his hair was standing on end and he just looked so damn perfect. Something primal in Dean sang knowing he’d done this to Cas—_Dean_ made him look like this. 

Without any argument Dean pulled the toy out of his friend and crawled off the bed to grab the larger piece. It was garish and pink and weighed his hand down significantly more than the other one, but the detailing on it looked so much more like a real dick. 

His mind was so kind to remind him how Cas compared it to his own and now Dean was about to put it into his best friend’s ass. He wasn’t going to survive this. 

As quickly as he could, he slathered lube all over it and brought it back to Cas’s entrance and pressed in, looking for any single sign that it might be too much. 

“Hngh—oh, oh fuck.” 

Dean stilled immediately again, worried as hell. “Is it hurting?” 

“S’big. Not—not hurting.” 

The way Cas’s eyes scrunched made Dean wonder if he was lying or not. It sent all of Dean’s aflutter. “Cas—I’m not sure—“ 

But Cas’s eyes opened at that moment and he sought out Dean’s hand once more. “Please? Want more.” 

There was a plea in Cas’s eyes and Dean couldn’t help but give into it. “Okay—“ he agreed again right before he pressed the toy a little deeper. 

“Ohh, mmm.” 

He’d never heard Cas sound like this, so vocal with need. 

“Fuck… are you sure?” He asked, feeling more overwhelmed than he had in a long time in the bedroom. 

“Yeah—yeah. Dean… Promise.” 

This time Dean kept his movements slow and kept his eyes locked on Cas’s face, making sure that his friend wasn’t showing any signs of discomfort whatsoever. It was when Cas’s hips started to press down to chase the toy and his friend’s hand was flying over his dick that Dean started to speed up his movements. 

“Oh—oh god. Oh god, Dean—oh!” 

He knew Cas was close. He couldn’t fucking wait to see this orgasm. “Come on.” 

His wrist was starting to ache but he didn’t let up even a little. 

“Yesyesyesyes---“ Cas half-whispered then suddenly those words were cut off by a silent scream. 

Dean pressed the dildo deep, right at that moment wishing more than fucking anything it was him who got to be inside Cas at this moment. That Cas could have wrapped himself around Dean and rode out that orgasm with Dean’s cock deep inside him. 

God Dean was jealous of a fucking toy because he wanted to feel Cas clenching around _his_ dick. Fuck. He didn’t know if he’d be able to keep his sanity much longer if he watched his friend come on these toys anymore and this was only the first time he got to see such a glorious fucking sight. What would he even do if he saw this for days? Weeks? 

There was no way he could survive seeing Cas so fucking perfect like this. 

Dean wanted him so bad it made him insane. 

He pulled the toy out of his friend and dropped it on the bed. He moved between Cas’s legs, hovering above him a few inches and took his own cock in his hand. As Cas laid below him Dean couldn’t help but stare at the come that had splattered on Cas’s chest and stomach. And like that Dean was blowing his load again, mixing his own release with Cas’s. 

He fell to the side, careful not to land on his friend. This time Cas was the one who pulled Dean into his arms. This time Dean was the one who buried his face in Cas’s neck. This time Dean was the one who fell asleep on his friend. 

This time Dean realized that there was nowhere he’d rather be and he was fucking terrified.

**Notes for the Chapter:**

> Thank you to everyone who has been commenting on this! I really do hope you're enjoying it. The next chapter will be nearly 10k so look forward to that while I try and force myself to edit it :P


	9. November 9, 2017

It’d been a week since they’d started using the toys and Cas was—enlightened. He hadn’t ever, for a second, thought having any sort of object up inside of him would feel incredible but he was pleased to be proven wrong. 

It wasn’t an everyday thing he indulged in, that’s for sure as he found it a bit of a hassle to be cleaned and ready to go each and every day, but the days that Castiel did ask for them to play around a little more with the dildos he usually managed to get two or three uses out of them. 

He definitely had a preference for the larger of the two but Dean still seemed hesitant to use it—like he was scared Cas wasn’t telling the truth about there being no discomfort. And, okay, maybe there’d been one time that there’d been too little lube used and it wasn’t the most delightful thing Cas had ever felt but he’d practiced using his communication skills and asked Dean to put more lubrication. See, communication. 

Still, Dean, being the assbutt he is, made it his mission to have Cas practically begging before he’d give into using the larger one. 

Dean was proving to be an even better teacher than Castiel had thought he would be too. They weren’t having actual intercourse but Dean made sure to give Cas suggestions on how to move his body—his legs, his torso, his arms—to make himself feel sexier, is how Dean put it. Dean helped him get over the slight embarrassment he felt now that his moans and groans were a touch louder than they had been previously; apparently Cas wasn’t allowed to muffle those noises because it was ‘beyond hot’ to some men. Dean even had him trying different positions to take the phallic toys. 

That had been an increasingly interesting time. Though Cas was eager to learn everything he could, he’d started to feel slight tendrils of vulnerability creeping in when they tried new positions. First Dean had asked him to bring his knees to his chest, something Castiel felt would be a simple change to the standard missionary they’d started with, yet, being on display like that made his mind race with too many questions. _ ‘Do I look stupid?’ ‘Does Dean think this is attractive?’ ‘Am I even attractive enough to do this with Dean?’_

He ended up asking to try a new position after a few minutes of Dean pumping the toy in and out of him. 

Being on his belly with a pillow underneath was a lot safer. He didn’t like not being able to see Dean but the trade off of not feeling so on display was comforting. Even Dean seemed to like the position, growing bolder in his wrist movements, thrusting faster and deeper than he had when Cas had been able to look at him. That fact in and of itself had Cas’s mind swirling again with thoughts though. Maybe Dean didn’t like looking at Cas. Maybe, he too, was more comfortable when he didn’t have to see Cas’s clearly _male_ face looking up at him. Maybe like this, Dean could pretend that Cas was some beautiful woman who Dean had taken home… Maybe Dean didn’t like when they did this together because Cas was always, without a doubt, staring up at him and Dean just didn’t want to look at him… 

He tried to stop but _not_ staring at Dean was hard. Not staring at the way Dean’s eyes seemed to darken with lust—enough so that Castiel could pretend that Dean was lusting for _him._ Not staring at the way those same eyes would sometimes travel all over his body, almost looking hungry for the skin they were staring down at. Not staring at the way, for the briefest moment, those eyes would lock with his own and Cas would melt into an them because it felt like Dean might want him too. Not starting at him in order to see those moments where his mind could trick him into thinking Dean might desire him back? He couldn’t help himself. 

It’s all Cas wanted at this point. 

When they’d started all this he just wanted to be wanted by anyone. But now? Being wanted by Dean and Dean alone was his greatest wish.

He knew it was futile and that never in a million years would he be lucky enough for Dean to actually have feelings for him but his heart just wouldn’t give up. His mind was no better. He knew, deep down that the logical thing in this situation would be to walk away but every time that fleeting thought rose to the surface, Cas found another excuse to stick it out. He knew he was bound to hurt himself. He knew he was treading too closely next to an abyss and one misstep would take him over that edge but all sense of rationally went out the door the minute Dean Winchester touched him for the first time. 

“Kiddo, you still there?” 

Castiel suddenly came back to himself. “Huh? What?” He asked over the phone, hoping beyond hope that he hadn’t muttered any of his previous thoughts aloud. 

“I asked if the three-hundred-dollar charge on your account was actually yours.” 

He couldn’t express how thankful he was that Gabriel was on the phone and unable to see the hot flush up his neck. Yeah… that’s why his mind had been wandering to the past three weeks of experimentation with Dean. 

It was Thursday, which happened to be the day his dad would generally call him to check in during the week, yet Castiel hadn’t expected him to bring up the charge on his account from three weeks back. Leave it to Gabriel to only notice something like that a few weeks after the fact. He knew Gabriel wouldn’t be mad about the money (they were pretty well off with Gabriel being a successful director) but Cas should have at least thought of some sort of excuse before he made such a big purchase. 

He figured truth by omission would be his best bet. 

“Sorry, I was—there was something on Facebook that distracted me. Uh, yes. That—that was me.” 

“Okay. Give me a heads up next time you spend that much so I don’t think you got mugged or something.” 

“Dad, that was nearly three weeks ago. I think you would have known if I were mugged by now. But I’m sorry…. I’ll remember next time.” Cas nearly wiped his brow with relief, getting out of that conversation.

But of course Castiel should have known Gabriel couldn’t help but be annoyingly nosy. 

“So what’d you buy?” 

He tried not to outright groan at the question but he kind of wanted to die. It was just another lie he was going to have to add to his ever-growing list. 

Castiel hated lying on principle. It was tedious to remember the details of every lie told and lying to the people he cared for didn’t make him feel great, yet he seemed to be doing it all the time now. Lying to Hannah about who he was seeing, lying to his dad about what he was spending money on, lying to Dean about the fact that Cas was completely enamored with him and wanted to kiss him and be held by him and… 

He hated lying but he continued to do it anyway. “Just—just some new clothes and some things for school.” 

“Cool, cool.” Gabriel replied, taking Cas’s words at face value. “Anything new and fun going on? Come on, tell me all about the raggers and orgies you’re going to. Any weeklong benders recently?” 

At least Cas could count on his dad’s lack of attention span. “Dad…” 

“I know, I know. I’m not funny. But seriously kiddo, the last few times I’ve called you’ve been pretty busy. I haven’t gotten to talk to you much.” 

“I know, I’m sorry.” 

“Don’t be. I know you’re having fun.” 

There was a hint of sadness in Gabriel’s voice that Cas knew he was trying to hide. It left him feeling guilty. 

It’d just been him and Gabriel all his life and Cas, even now, struggled with being away from him. He’s still not sure why he picked going to UNLV over any of the universities he could have attended in California but something about the school had felt right for him. He almost didn’t go, to be honest; not wanting to leave his dad alone. He’d even tried to convince Gabriel to move with him to Nevada but Cas knew Gabriel’s career was in California. It’d been hard, and at least he had Dean and Hannah to get him through, but he still missed his dad more than he could explain. He knew he needed to make more of an effort to talk to him. 

“I should still make more time to call you. I’m sorry.” 

“Stop that. I’m fine. Really.” Gabriel insisted. Cas could hear it in his voice that he didn’t want Cas feeling guilty. 

“Is Kali still living there?” Cas asked, mostly out of politeness. 

“Uh—kinda. We uh, we got in another argument.” 

“About what?” 

“Nothing to worry yourself with.” 

Cas instantly knew what it was about. It was the same pattern without fail. 

“It was about me again wasn’t it?” He knew Gabriel tried to keep that stuff from him, but there was only so many times Cas could hear _‘You always pick him over me,’_ and not know what they’d been fighting about. 

“It’s no big deal. I should have learned from the last hundred times she’s done this that she is never actually going to be cool with me having a kid. She just keeps convincing me that she’s really changed and that she’s fine with it but then she goes and throws a fit. Asking me why I’m not taking her on round the world trips when she knows I can’t just pick up and go. That I don’t _want_ to pick up and go.” 

“But you _can_ just pick up and go now. I’m away at college, I’d understand if you’d want to travel around with your girlfriend and have the time of your life you never had because of me.” 

“Don’t say that.” 

“But it’s true.” Castiel insisted. He hated that Gabriel had to forfeit some of his dreams because he had to take care of Castiel. He hated that Gabriel’s directing opportunities were mostly limited to only California because he couldn’t travel to another state or country for extended periods of time because of Castiel. He hated that Gabriel still kept putting his life on hold because of Castiel. “You told me you used to dream of drinking your way through Europe.” 

“Yeah, well, I was eighteen then. Things change.” 

“You could have the time of your life.” 

“I’m having the time of my life now.” 

“There are movies and shows you’ve turned down because of me. Now you can do them. You _should_ do them.” 

“You’re right, I can accept those jobs, and I will for a few of them but I’m not just going to jump from place to place and live in hotels for the rest of my life like Kali seems to want. 

“But it _is_ what you want.” 

“It’s what you _think_ I want, kiddo. What I really want is to have a place for you to still call home whenever you come around. I know you might think it limits me but it’s what I want. You’re not going to change my mind. Okay? Your home is here and so that’s where I’ll stay.” 

“Dad…” 

“Nope. We’re not going to argue. We’re going to change the subject. So, uh, are you coming home for Thanksgiving or are you spending it at the dorms with Dean?” 

Cas felt himself pouting a little at the forceful change of subject but he tried to hide it in his voice. “Dean said his brother might be coming out that week and wants some tours of the campus. I volunteered to take him around.” 

“So you won’t be home then?” 

Cas couldn’t just ignore the ounce of sadness he detected in Gabriel’s voice. “Is that okay?” 

“Yeah, kiddo. It’s your call.”

He knew that was the universal parental phrase for ‘I’m trying to let you make your own choices but I wish you would pick my choice.’ He knew Gabriel was a little lonely now that Cas was a state away. Growing up was just so hard. Balancing a life between the friends he loved to spend time with and the only family he had, was hard. He found himself wishing he could easily have them all in one place. 

“I miss you.” Cas said honestly knowing Gabriel needed to hear it. 

“I miss you too.” There was a pregnant pause between them before Gabriel asked, “You’re probably going back with him for Christmas too?” 

“We haven’t talked about it.” 

“If you do… maybe you could stop by home for a couple of days or a week? If you want.” 

And as much as Cas loved the idea of spending the holidays with Dean, cuddling in the winter coldness, exploring a little more under the cover of their blankets… Castiel knew he needed to go back home. 

“I’ll be home. I promise.” 

“Go have fun kid. I’ll call you next week, okay?” 

“Okay.” 

Castiel frowned into the phone. He knew his dad well enough to know that Gabriel was just trying to run away from an emotional conversation—he was much like Dean when it came to that stuff, funnily enough. 

“Love you.” 

“I love you too.” 

When Gabriel finally disconnected the phone call, Castiel sank back into the futon and moped a little. He even decided to get in an episode of Grey’s Anatomy before Dean got home to cheer himself up. He could only watch it secretly, knowing how Dean felt about the show. (_How dare you? You’re cheating on Dr. Sexy!_). He smiled to himself and checked the time, hoping that Dean might get home earlier than usual today, just so Cas could spend a little more time with him. 

He realized then just how pathetic he sounded and felt embarrassment creep up his spine. As always he was waiting around just for Dean to come home. Even before they’d started their little arrangement Castiel would find himself counting down the minutes until his friend got home. Now though, with the added benefit of there being a lot more naked bodies and infinitely more touching, he couldn’t help himself from counting down the seconds until Dean walked in the door. 

He was starting to wonder if he was getting pathetic. Scratch that, he knew he was pathetic. 

Dean had so many friends, all who were vastly a better use of his time than Castiel was. He didn’t mean it self-deprecatingly, but it didn’t make it any less true. Dean’s other friends were funny and exciting. They told jokes and talked animatedly about anything under the sun, and easily at that. They went out and met people and always had an adventurous time. They didn’t choose to shut themselves in on most days or spend their time just watching TV and browsing the Internet. They were _normal._

And Castiel was the opposite. He always wasted Dean’s time, keeping him home to just watch a movie or TV. He’d find random YouTube videos or other Internet things and force his friend to watch them along side him for hours on end sometimes. And no, Dean never seemed to mind that he was being forced into that stuff, but Castiel knew that Dean couldn’t be _thrilled_ with him for it. 

He knew that he should let Dean have some space. Cas had Hannah he could hang out with, or Meg and Balthazar on rare occasions when they weren’t off prowling through parties that Cas didn’t really feel like attending anymore. He just—he didn’t want to hang out with anyone as much as he wanted to with Dean. Something settled in him when Dean was around, it had been that way since they had first met, and Castiel didn’t want to give that up. At least now he had something to offer his friend in return. 

Deep down he knew that Dean didn’t _seem_ to mind hanging out with Cas’s uninteresting self, but it didn’t stop him from wondering if Dean ever felt bored with him. His friend would never say, of course, because he was too polite… but Castiel had a deep-seated fear that maybe he was too dull to keep Dean as his friend for much longer. He figured though that the added dynamic of he and Dean fooling around at least gave Castiel a leg up in keeping Dean around. Right? 

That’s what Castiel hoped, to say the least. 

He just didn’t know…. 

Was this a mutually satisfying arrangement they had going on? For Castiel it absolutely was. He couldn’t get over just how amazing everything felt. Even just seeing the way Dean came undone when Castiel touched him, that was satisfying in and of itself, but now? Now with Dean’s hands on him more, now with Dean fulfilling some of his fantasies, touching him, fingering him, bringing Castiel to orgasm even with the use of toys… it was incredible but was it as fulfilling for Dean?

It seemed like it was. It felt like Dean was as into it as Castiel was but perhaps it was all just the heat of the moment? How could Castiel tell if Dean just liked the sexual acts or if he liked the sexual acts _with_ Cas? It was safer in Cas’s mind to convince himself that Dean just liked the pleasure he received and nothing more…

Whatever it was, it didn’t matter, Castiel just wanted to take in all that he could for himself. He wanted to be selfish and have all he could with Dean because he knew all too soon it’d be taken away. More than anything he didn’t want it to end. He didn’t want to go without Dean’s hands on his body or vis versa. He didn’t want to think about anyone else ever touching the body that he’d grown so accustomed too, the one he craved all day. The body he could so easily picture each time he closed his eyes. 

And dear lord did Dean have a wonderful body. He’d been thin when they’d first met, Castiel even remembers thinking he’d been lanky—especially so when he’d wear an old hand-me-down leather jacket that seemed two sizes too big. But now he was taller and broader in a way that seemed to have just happened overnight. One day he was lean and all bone and the next moment Castiel was peering over at his friend with wide shoulders and muscled arms. He hadn’t paid much thought then but now he couldn’t stop paying attention to it. 

Dean wasn’t one to brag about his fitness, and despite the lazy persona and the overindulgence in all foods, his friend actually cared about being in shape. Both Benny and Victor dragged him to the gym often and Dean even went by himself on occasion and it paid off. Castiel wasn’t immune to what a little bit of muscle mass could do for a person. 

Even now, just sitting on the couch trying to pay attention to what was on TV, Castiel couldn’t stop his mind from swirling with thoughts on how incredible it might feel to have his friend manhandle him just a little. How thrilling would it feel to be picked up by those arms? How delicious would it be to feel the muscles in Dean’s thighs as he pressed up against him, or… inside him? What would it feel like to grip Dean’s ass? Or to be flipped over until he was on top of his friend, able to feel all of Dean’s chest and stomach without shame? 

He was insatiable and it was all Dean’s fault. 

He tried to shake the thoughts out of his mind before he got too pent up with want. He tried to not allow himself to get too eager, just incase Dean didn’t seem to be in the mood. At least it wasn’t too hard for Castiel to get his mind off Dean’s good looks with his conversation with Gabriel still in the back of his mind. 

He had to remember to talk with Dean about winter break plans. 

Castiel was maybe halfway through the Grey’s Anatomy episode when his friend walked in and dumped his backpack on the ground by their door. 

“You’re kidding me right?” 

By the look of his friend’s ‘shocked’ face, Castiel could tell he hadn’t managed to exit out of the show quick enough. 

“Hello, Dean. How was your day?” 

“Good… besides the fact that my best friend is a giant traitor. Watching Grey’s Anatomy in my own home.” His friend shrugged out of his hoodie and kicked off his shoes before heading over to the couch with a smile on his face. When he got close Castiel could hear the sound of something packaged in Dean’s hand. “Hey, I got you this.” 

Out reaching his hands, Dean offered Cas a packed Honey Bun, icing sticking to the inside of the package as expected. 

“You did? Why?” 

Dean shrugged. “I know you love them so when I saw it I just grabbed it. No big deal.” 

“Thank you.” Castiel tried to not feel downright smitten over a dollar treat but his emotions were acting a bit fickle. Damnit, his emotions were a mess lately. As much as he tried to fight it, everything kind Dean did for him: running after Cas to give him his forgotten coffee thermos, flipping the channel to a documentary Cas had been interested in, rubbing his back as they cuddled, or bringing him a damned Honey Bun—everything made Cas’s insides turn to mush these days. 

He really was pathetic. 

“It’s no biggie.” 

“Do you want to share it?” 

“Hell yeah.” Immediately Dean plopped down onto the couch besides Cas as he tore into the treat, ripping it in half and of course, giving the bigger piece to Dean. “So, whatcha been doing today besides being a Dr. Sexy traitor?” 

“Nothing really. I talked to my dad earlier though.” 

“Yeah?” 

“Yeah.”

“You okay?” Dean asked suddenly, picking up on signals Castiel didn’t realize he was emitting. It was pretty seamless how well Dean seemed to read Cas. 

“Oh, yeah, I’m okay, I just miss him.” 

“I get that.” 

“You do?” 

Dean sank further into the couch until he and Cas were shoulder to shoulder. His green eyes peered over at Cas and gave him an understanding smile. “Yeah I do. Well you know Sammy’s coming out here soon and I’m real glad I’ll be seeing him but part of me wishes it was all of them. I miss Jody and Bobby too. You know?” 

“I do.” 

“It just sucks that missing our family is a feeling we just have to live with now. Like… I know I’m never going to go live back in South Dakota so I just have to deal with missing them all the time now. It sucks. And you’ve been with just your dad since you were a baby, it’s probably hard being away from the most important person in your life.” 

“It is.” Cas frowned. “I guess it’s comforting to think that I only have this year before I go back… I’ve always pictured myself moving back home after school so I’ve known the distance between myself and Gabriel would be just until I graduated.” 

“See, in no time you won’t have to miss him.” 

“But you don’t think you’ll move back home after we graduate?” 

“No, it’s not for me. I like it there but I want to do something more with my life, you know? Really it all just depends on where Sammy moves, too. I don’t want to be that far from him.” 

Cas felt a wave of melancholy wash over him at the thought of he and Dean parting someday. He knew it was always going to be the case. He knew how close Dean and Sam were and that even being away at college was hard on Dean. He couldn’t picture the two brothers living this far from each other for much longer if they didn’t have to and it just so happened to work out that Sam would be entering college when Dean was graduating. 

Still, it didn’t make Cas feel any less sad about that impending date. What would it be like to not see his best friend every day? What would he do without their talks and just the comfort of having someone on his side? He didn’t like the feeling but he tried to squash it down. 

“Hasn’t he mentioned wanting to move to California?” 

Dean nodded his head with a proud grin. “Yeah. I think he’s pretty set on it, unless an Ivy gives him a scholarship.” 

“Well if he does decide on California then maybe that means we’ll both end up there.” 

He couldn’t hide the hopefulness in his voice even though it was all wishful thinking—idealistic and silly even, yet Castiel still painted a picture in his mind that maybe, just maybe, he’d manage to keep Dean a little longer. If they were moving to the same state… maybe they could stay close. Maybe they wouldn’t lose touch at all. 

“Yeah, maybe it does.” There was a smile in Dean’s eyes that made Cas’s heart flutter, just a little. 

He fiddled with the idea of suggesting that he and Dean continue living together if they both were to wind up in California but thought better of it. He didn’t want to back Dean into some sort of corner. Besides, Dean probably would much prefer to live with his brother opposed to Castiel. 

Before Castiel could dwell on the thought for too long, Dean spoke up again. “You wanna go out for dinner tonight?” 

“That sounds nice. Do you have something in mind?” 

“I could go for a burger and fries.” 

“I’m in.” 

It took a few minutes to decide between going to an actual restaurant or grabbing some fast food but eventually they decided on In-N-Out Burger and headed there on foot. The walk wasn’t long but Cas’s stomach was definitely rumbling loudly by the time they got there. He didn’t even need to speak once they got to the counter since Dean already knew his order by heart: a double-double animal style, animal style fries, and a Neapolitan shake. The only difference in Dean’s order was the preferred strawberry shake. 

Again, Cas tried not to swoon a little when Dean said, ‘my treat,’ right after the employee told them the total. Once they had their orders placed they found a booth and waited for their numbers to be called, and filled the wait time with talking about anything that came to mind. 

“Is Hannah still at her internship?” Dean asked. 

Castiel nodded, remembering back to the stream of un-Hannah-like texts she sent when she told him one of the new interns had messed up and had wound up putting double the work on Hannah’s shoulders. Apparently interning at a publishing house was not an easy feat. 

“She is.” 

“She liking it?” 

“From what she’s said, she does. On most days.” 

“Does she think she might be able to land a job there once she graduates?” 

“She said her supervisor seems to favor her but no one has really mentioned any openings.” 

“Hopefully they’ll want her.” 

“She’s good at what she does.” 

“Seriously. She’s the most organized human I know. She’d be kickass at literally any office job.” 

An employee’s voice broke into their conversation. “Order 15!” 

“That’s us.” Dean said with a grin and jumped up from the seat to get the food from the counter. When he returned he plopped the tray in front of Cas and started unloading the items in front of their seats.

“Did you get—“ Cas started to ask but was cut off by two packages of spread being flopped onto the plastic table in front of him. 

“Two extra packets.” 

“Bless you.” Castiel said gratefully, trying to hide his blush at the wink Dean sent his way before taking the tray to the trashcan. 

Once Dean was back in the booth and they had their food in front of them, the conversation came and went without much rhyme or reason.

“Did you do your discussion board posts?” 

“I did. Finally.” 

Dean groaned. “I hate them so much.” 

“Yet every professor makes us do them.” 

“Assholes.” His friend mumbled which Castiel silently agreed to as he chomped into his burger. Dean was equally as inelegant in his eating, speaking next around a mouthful of food. “Dude, can you believe we’re graduating this year? Like how did that happen so soon? What even happens after that?” 

“Adulthood.” Cas replied mournfully. 

“See, that shit is unfair.” Dean exclaimed, waving his burger in the air. “Like how am I expected to know how to do all that adult shit. I’ve never done my own taxes. I don’t really know what a mortgage is. I don’t know how to open a freaking savings account. Like how can society just expect me to know this shit when we weren’t taught any of it in school?” 

“I assume natural selection is generally in play. Only the strongest will survive.” 

Castiel smiled when Dean barked out a laugh. 

“If that’s the case then I’m gonna be dead real quick.” 

“You at least have a degree for a marketable skill.” Cas groaned. The prospect of his future was often a dreaded topic. “What was I thinking studying _languages?”_

“You’re marketable.” The way Dean said it made Castiel glare. 

“Oh, you think being your go to person for saying ‘can I buy you a drink’ in other languages is marketable?” 

“Je t'offre un verre?”

He tried to deadpan as hard as possible but the cheeky grin on Dean’s face made Cas crack. “At least you’ve managed to remember one thing I’ve taught you.” 

“When it comes to pick up lines, I have a great memory.” 

“Of course you do.” Cas rolled his eyes and took a bite of his fries before he sighed a little. “In all seriousness, I have no idea what I can even do after graduation.” 

“You’ve talked about being a translator. Have you looked into that at all?” Cas shook his head at the question. 

At the time of picking his degree, it had sounded like an awesome idea to study languages. Gabriel’s grandparents spoke Italian so he passed the language along to Castiel as best as he could. Castiel’s mother had loved the French language, according to Gabriel, so in her honor Castiel took that throughout high school. He seemed to have a knack for picking up each language and was fascinated by the way they worked so the degree just made sense. But now? Now he had no idea what he could do with it. 

“I don’t have enough experience with social conversations. I mean Gabriel spoke in Italian to me a lot but not enough that I could translate common slang and everything else that might be asked of me.” 

“You read it and write it pretty well though. You could translate written work and stuff couldn’t you?” 

“Maybe…” 

Dean must’ve sensed the underlying frustration Castiel was trying to hide. He knew logically he’d find work somewhere, perhaps not in his field of study but somewhere. The idea of an uncertain future made him anxious though. Bless his soul, that Dean Winchester, for knowing when Castiel needed to laugh instead of stress. 

“I’ll just be your sugar daddy. Don’t worry. I got you.” 

“What would I do without you?” 

“Te moririas.” 

“Changed my mind. I can’t wait to be rid of you.” He said the words with a smile although it was obviously a lie. Dean played along anyway. 

“You wound me.” 

Cas half groaned, half laughed into his hands. “Honestly, I’m just not ready. I’m glad we have more than six months. I keep thinking about what it’ll be like to live with someone else too and it’s very off putting.” 

“Because I’m the best.” 

Cas let out a laugh. He didn’t know what to say. Dean _was_ the best and Castiel was going to be lost without him. 

Perhaps Dean felt similarly. 

“But really, Cas, I’m not really looking forward to not living with you either. We work together pretty well I think.” 

“We do.” 

With the mood a little somber, neither boy said much else until Dean started gathering their trash. “You wanna head out?” 

“Oh. Yes, sorry. We’ve been here a while.” 

He didn’t protest when Dean insisted on cleaning up for them and he definitely didn’t protest to the softest pressure of a hand he felt on his lower back as they exited the restaurant. If, just for a moment, Castiel let himself fantasize that this was a date then that was his secret to keep. 

As they walked back towards their dorm Castiel wished that he was able to ask Dean to just lie with him in bed and hold him for the night. Perhaps Dean would even say yes, because Dean was too kind a human to turn Cas down outright but Castiel knew that wasn’t in their arrangement. He knew that he only got to feel the comfort of Dean’s arms after they fooled around. He just wasn’t sure if the night would result in any sort of ‘learning,’ though. Somehow he doubted it. 

He probably brought down the mood too much being sad about Gabriel, making Dean sad about his family, talking about moving away from each other and the stresses of impending adulthood. He wouldn’t be shocked if Dean didn’t feel up for anything for the night, as badly as Cas was craving touch. 

It was alright though. There was always tomorrow. 

But damnit he wanted to be held so badly tonight. 

They got back to their dorm and quietly went about getting ready for bed. Dean was first to jump in the shower, which left Cas to pitter around the room and clean up a little. By the time Dean was out, a towel wrapped around his waist, Cas had cleaned up a lot of the week’s mess and slid past Dean to take a shower of his own. He spent a little longer in the shower than he had planned but felt compelled to wash himself thoroughly just in the off chance that Dean decided to touch him. 

By the time he came out of the bathroom, hair still wet but a pair of pajama bottoms on, he expected Dean to probably be asleep. Instead he found his friend just resting on the couch with his feet up, the TV off, and the room quiet. 

“Not watching TV?” Cas asked, shuffling from where he’d dropped his dirty clothes in the hamper over to the makeshift living room.

“Nah. Don’t really feel like it.” 

“You just going to bed then?” 

There was a glint in Dean’s eyes that Castiel hoped meant what he thought it did. “No. I don’t want to go to bed.” 

Cas felt warmth build up in his chest as he read the words Dean wasn’t saying. He found himself being drawn towards the empty space on the couch and sat down next to his friend, looking over his left shoulder to smile at him. Only the light from the bathroom was on so the warm hue of the light paired with the shadows across Dean’s face made the other man look positively enchanting. 

Castiel didn’t know what to say but heard himself mutter a small, “Hi.” He cringed at the stupidity of that singular word but apparently Dean didn’t seem to care as he said the word right back. 

“Hi.”

There was something charged in the air that left Cas’s limbs trembling in anticipation. The way Dean was looking at him like he knew just how badly Castiel needed those hands on him… Cas didn’t even hesitate to ask, “Do you wanna…?” 

“Yes.” Dean’s response came out in a huff of breath and Castiel reacted almost immediately.

“Me too.” 

The moment didn’t call for frantic removal of clothes but Castiel sank to his knees quickly. He pulled himself together a moment later, feeling the urge to draw this out as much as possible. First he’d just let himself touch. Much like the time all those weeks ago, he let his hands roam where he thought best. But now—now he understood Dean’s body so much more, so much better. Now he knew the way Dean’s eyes would darken when Cas pushed his thighs apart. Now he knew the right pressure to use because light pressure made Dean ticklish. Now he knew just the way to grope his friend, firmly through the front of his pants, and Cas wasted no time in giving him what he wanted. He, himself, just… wanted. 

He almost felt on autopilot—not going through the motions but, instead, feeling almost seamless in his actions. He wanted to see Dean fall apart. He’d categorized every way he’d been able to make Dean breathless and was using them all now. 

He used his hand for a little while, just long enough to feel Dean’s stomach tremble before he lowered his mouth around him. His friend wasn’t yet fully hard but Castiel didn’t mind spending some extra time using his mouth. He loved that he got to get Dean hard, it was when he hallowed his cheeks and sucked on the flesh in his mouth, feeling it grow as he continued to bob his head up and down, that he knew Dean was getting hard for _him._ And even if Dean were fantasizing that Cas’s mouth was that of some no-name women, it didn’t matter because it was _Cas’s_ mouth who got him there. 

That thought had him moving with more of a purpose. Weaving and bobbing his head as his mouth moved up and down Dean’s shaft, relaxing his throat just enough that he could suck from base to tip in one delicious stroke. 

“Holy fuck. Yeah. Like that.” 

Castiel continued the same motion, up and down, bob and weave, doing everything he could to get Dean off. He knew it’d be so worth it, tasting Dean on his tongue then knowing that Dean wouldn’t let him go unsatisfied. He didn’t need the toys tonight, he didn’t need Dean to even touch him but if his friend just happened to want to, Cas wouldn’t complain. More than anything he just wanted what would come after, just lying in his friend’s arms. 

Dean’s fingers found their way into his hair, and Castiel groaned his approval. He loved when Dean would guide his mouth just the way the other man wanted. Only, this time that didn’t come. Instead of thrusting his hips up into Cas’s slack jaw, Dean pulled him off of his cock. 

“On the bed.” Dean commanded, looking down at Cas with flush cheeks. All Castiel could do was nod. 

He strode with unstable knees to Dean’s bed and climbed on, feeling Dean merely inches behind him. 

“Lay down.” 

Castiel complied immediately, feeling his breath pick up the moment his back hit the sheets and he felt Dean’s fingers hook under the waistband of his pajamas. 

“Roll over.” 

Again Castiel obeyed quickly, adjusting himself on the bed as he waited for Dean to grab the toys and lube. As always his heart rate started to pick up in anticipation, counting down the moments until he could feel Dean’s broad hands against his skin. 

Dean didn’t make him wait long. Mere seconds after Castiel felt the bed shift to accommodate Dean’s weight, he felt those hands on the back of his thighs. His back automatically arched from the touch, knowing that in moments Dean’s fingers would be right where he wanted them. He could hear the click of the bottle of lube and shivered in eager anticipation. 

Then Dean’s fingers were there, trailing down the crease of his ass and circling his rim. He hummed a delighted sound against the pillow at his cheek. 

Cas could feel the pad of Dean’s thumb trace over his hole and he waited with bated breath to feel the tip of his finger breach him but that didn’t come as soon as he hoped. Instead he felt the same thumb move over the surface of his skin as Dean croaked out in a wrecked voice, “Did you shave?”

The heat of embarrassment rolled down to the base of his spine as he kept his face buried in the pillow. 

“I—I yeah. I just thought... it’s—it’s stupid isn’t it?” 

He didn’t know what the hell he was thinking. He did it in the spur of the moment in the shower after he’d been thinking about it for a few weeks but maybe he made a big error in judgment. It’s just… he didn’t know if it was exactly sexy for him to be more on the natural side. Before he didn’t care but now… now knowing that he had Dean’s eyes on him more often than not, he didn’t want to be undesirable to the other man. Dean didn’t seem bothered by his previous grooming choices but he feared his friend would be too nice to share his legitimate preferences. 

“No. Not stupid. It looks good.” Dean’s fingers were still smoothing over his entrance, refusing to push in. 

Cas couldn’t help but voice some of his insecurities, feeling safer with his face hidden from view. “Is… is it better like this?” 

“It doesn’t matter to me.” Dean replied gently. “However you like it.” 

“I just thought… maybe you’d like it…” 

“I like it however you like it.” Dean cut him off, pressing the tip of his finger past the tight ring of muscle. “Tell me, do you like this?” 

“Yeah.” Cas huffed out quickly, his eyes fluttering shut at the feel of Dean’s finger pressing deeper. 

“Good.” His friend whispered back before pressing more urgently into Cas’s body. 

His friend worked quickly but not as quickly as Cas would have liked, even after repeatedly assuring Dean that he was ready and, “Just put it in me. I’m prepped. I swear. Dean, please.” 

When finally, _finally,_ the head of the toy breached his entrance, and the weight of Dean’s hand landed on his spine Castiel let his mind go. There was something in the room, in the air, in the space between them that let Castiel simply melt into the moment, allowing himself to just be consumed by want. 

The way he wanted Dean. The way he wanted everything he could get from Dean. 

The way he wanted Dean to want him. 

It twisted through his mind like a hurricane. _Want me, want me, please want me back._ And Castiel didn’t know how to slow it down. 

He could feel the thickness of the toy moving in and out of him. He could feel the way Dean’s palm smoothed up and down his spine. He could feel the sheets beneath his fingertips, the sheets that had soaked up the smell of the man he craved. He let the sensations sink into his skin and he allowed himself to pretend that Dean felt as enraptured by this as he was. 

He knew that wasn’t true though. He knew that Dean’s good soul compelled him to make Castiel feel as good as possible too—that somewhere Dean felt that he owed Castiel some pleasure in return for the pleasure Castiel bestowed on him… it wasn’t ever because Dean craved Castiel in return. 

But when—when Dean moved to straddle one of Cas’s legs to get a better angle of his wrist—Cas couldn’t help but notice the thick cock pressing against the back of his thigh and in the brief moment he thought _maybe…_

Maybe the feeling in the air was really there. Maybe he wasn’t a disillusioned basket case. 

Maybe Dean was actually turned on by the act of fucking him with a toy... of giving Cas pleasure too. 

Then it happened again, the feeling of Dean rutting against the back of Cas’s thigh and it couldn’t… it couldn’t just be a coincidence. 

But what if he was wrong? He could just be wrong…

Dean, after all, was a sexually virile man in his young twenties. Of course he was turned on by the prospect of engulfing his cock in any tight, warm flesh. 

But…. but if his breathing were anything to go by, he was definitely affected by the way Cas fucked back on the toy, begging and pleading for more. 

_Cas._ Not some random flavor of the night. 

Maybe—maybe Dean was reconsidering the use of strictly sex toys. Maybe Cas didn’t have to keep being in his head imagining that the cold rubber inside of him was actually that of a solid, warm human body. Maybe he didn’t have to keep pretending that he was feeling _Dean_ fill him up and use his body for his own pleasure. Maybe he could actually have Dean—maybe—

He couldn’t keep it in. All he was, was want. The center of his being was want. 

No…

It was need. 

“Dean!” He croaked out. His whole body trembled as he hovered now on his hands and knees, feeling Dean press the toy in and out him. “Dean! Ugh, more, I need more.” 

“You’re taking it perfectly. Just keep doing that. Yeah, keep pushing back.” 

Dean’s cock was against the cheek of his ass and all Cas could think about was replacing the imposter currently inside of him with the thing he wanted most. He was so far gone that the words had no chance staying in his mouth. “I want more. Please. Dean, fuck me. God, I need you to fuck me.” 

There was an undeniable groan behind him and an even more obvious stutter to Dean’s wrist. “Shit…” 

Cas slowed down the movements of his hips, not realizing until now just how much he’d been fucking back on the toy. He drooped his head to gather himself for a moment before looking over his shoulder, not quite making eye contact with Dean. He knew his voice was timid but he knew he at least needed to ask… 

“I know you want to. You can’t hide that you want to.” He knew he was grasping at straws but he couldn’t let this chance go by. 

“I can’t…” Dean whispered. 

“You can. I want you to. Dean, fuck me, please?” He fully looked over his shoulder and gazed into his friend’s eyes. There was pure terror in those emerald greens and it made Cas’s heart clench. 

“Cas…” 

“Please.” 

They stared at each other for a moment, neither saying anything and Cas knew he’d fucked up. He pried his eyes away and looked down at the pillows in front of him. He probably looked like such a whore. Ass up, a dildo still sticking out of him, begging for a dick… Why would Dean want to fuck him anyway? 

Dean moved away at that moment, pulling the toy out of him and Cas let himself completely deflate…. Of course he’d gone and ruined everything between him and Dean. Everything had been going so well but now he had to go and make everything awful. He was trying to find the right words… how to apologize to Dean and make everything right again when he felt an arm wrap loop under his chest and pull him up onto his knees. 

Dean’s chest was suddenly to Cas’s back, skin burning hot against Cas’s own. Cas instinctively reached a hand back, landing on Dean’s thigh, feeling the lightly haired muscle that he’d been fantasizing about touching. 

The scruff along Dean’s jaw scraped at his ear as Dean’s low voice spoke. “I need to know this is what you want.” 

A lungful of breath rushed into his chest and Castiel leaned back into Dean’s solid form. “I want this. I want you.” 

“How do you want this?” 

Castiel gulped, knowing that he only had Dean by a thread. Any misstep would make this all go away. More than anything he wanted to roll over and insist that Dean take him missionary but he knew that would be too intimate… to needy. He already knew Dean struggled with him being a man so he didn’t want to relegate Dean to staring down at his impossibly male features as he fucked him. 

Instead he fell back to his hands and knees, knowing this was probably what Dean would prefer. “Like this… This is good.” But to his surprise, Dean _wasn’t_ pleased with that choice. 

“No, turn around. Your first time shouldn’t be on your hands and knees.” 

“Dean, it’s okay.” Cas insisted, not wanting to fuck this up for himself, but the protest was futile. Dean gripped his hips and rolled him over. 

“Lay down.” His friend commanded, looking determined as hell to make sure that Cas was taken care of. 

Everything was trembling, the sheets, the pillows, everything around felt like it was shaking before he realized that it was himself that was shaking. He tried to control himself but the way Dean was propping pillows around him and not actually fucking him yet made the anticipation of the whole thing consume him. 

“Comfy?” His friend asked after finally getting the pillows arranged under Castiel. 

“Yes.” 

“Are you sure?” 

“Yes, I’m comfortable.” Castiel insisted, observing the doubt in his friend’s features. Cas was still so scared that this moment would be ripped from him too soon, they were so close, but Dean’s eyes shown with uncertainty and fear. 

“I meant… are you sure this is what you want?” The other man seemed to be pleading and Cas’s insides softened. His friend’s soul was so kind, so nurturing, that there was no doubt in Cas’s mind that this was the man he wanted to share his first time with. 

“I’ve been sure for a long time now.” 

That seemed to settle something inside of Dean. “Okay… okay, yeah. Good.” He didn’t waste much time then almost as if he was trying to not talk himself out of it. He lowered himself down just enough to move Cas’s legs high around his waist, pressing his cock against the crack of Cas’s ass. 

The anticipation of the moment left Cas shaking, gripping at Dean’s shoulders with every pass of the tip. But Dean refused to press in right away, almost as if he was waiting for Castiel to change his mind, and knowing Dean that’s exactly what he was waiting for. But Castiel was certain in this. So he impatiently waited as Dean took his time teasing, rubbing against Cas’s entrance as Cas writhed beneath him. 

“Please, please, please.” Cas finally begged, unable to dampen the primal need within him.

It was almost more than he could bear. He just wanted this moment. He just wanted to know that he had all of Dean just then, in their small bedroom, right then… he just wanted it all. 

“Dean,” Cas pleaded again and this time his pleas were not unheard. With one movement  
Dean was inside him, inching in slowly until he managed to bottom out. 

Castiel’s eyes fluttered shut. He had no idea. 

He had no idea it would be like this. 

How overcome with the thought that someone was _inside_ him… that Dean was inside of him, would make him feel. 

He gulped up breath as he felt Dean pull back out before pressing in. 

Cas’s eyes flew open then, craning up his neck to just look at the face of the man above him. Even though Dean’s eyes were closed Castiel felt that feeling of contentment he’d long contributed to Dean, wash over him as his friend moved. 

It felt better than he imagined it would. So much _more_ than the impersonal toy he’d had been using. No this—this felt amazing. Not just the feeling of a real cock inside of him but the warmth of a body pressed against him. The softness of flesh and muscle beneath his hands. Amazing. So fucking amazing… and all he felt was intense hunger as Dean moved in and out at a steady pace. Still so gentle with him but Cas wanted more, he wanted everything. He could feel his toes curling and his back arching every time Dean pressed back in. 

He couldn’t help but cry out, “Dean,” in that moment. 

He was surprised when Dean’s eyes opened and looked down at Cas, only briefly before they closed once more. 

“Is it good? Do you feel good?” 

“So good.” 

Dean’s groan was all the response he needed but Cas relished in the words Dean mouthed against his neck when his head drooped down to press into the crease between his neck and shoulder. “You feel so fucking incredible.” 

Cas turned to liquid goo hearing that. It was _his body_ that was giving this pleasure to Dean. It was _him._

His arms gripped tighter around his friend, as he moved similarly to the steady pace of Dean’s wrist with a toy but Cas knew he needed more than that. His body was practically ready to explode with his need but he couldn’t get there unless Dean gave him all he could give. He wanted more so fucking badly. 

“Dean… Can you… can you go faster?” 

“Faster?” 

“Please.” Cas whispered desperately clawing at Dean’s back. 

It might’ve been the little scratches or the pleading tone but something seemed to snap inside Dean then because suddenly he didn’t hold back. The movement of his hips felt almost wild and he tried to bring his pace to what his wrist had been achieving only minutes earlier. 

Maybe he could have thrusted even faster if Cas wasn’t wrapped around him like an octopus but Cas was unwilling to unwind his legs from where they were locked high behind Dean’s back. And he certainly wasn’t about to move his arms from where they were wrapped around Dean’s broad shoulders, allowing his hands to feel the muscle of Dean’s upper back. 

He clawed a little more at his friend’s muscles as Dean finally managed to get the right leverage to move at a mind-melting tempo. 

Cas’s mind was racing. 

It felt amazing. 

It felt so fucking good to feel someone moving inside him. 

Inside him…

Holy shit. 

He just lost his virginity to Dean. Dean, his best friend would forever be the first person to ever be inside him. 

The realization hit him and he couldn’t help but gasp. 

This… this was a moment. This was a big deal. And it felt…

Perfect. 

“_Dean!_” He practically wailed as his friend thrust hard and deep. 

“Oh fuck. Was that—Was that okay?” 

“Yes! Yes! Do it again.” Castiel felt almost out of his mind. It was racing and it was a blur and it was overwhelming and holy shit this was actually happening. “Uhn-fuck. Uhn-_Dean._” 

“Shit. The way you say my—shit.” The small nip to his neck made Cas gasp. “Shit I’m too close.” 

Dean suddenly pressed his upper body away from Cas making him protest greatly. 

“What? Why?” 

Green eyes were suddenly peering down at him, completely lust-blown. Dean’s chest was rising and falling with what looked like great effort. His thrusts became slower, shallower. “You need to come. Come on. Touch yourself.” 

Cas could see that Dean was completely on the edge, hovering on his knees as he pressed in and out of Cas’s hole. Both of Dean’s hands were gripping at the back of Cas’s knees, pressing them up and back to get the best angle he could and there was nothing Cas could do but fulfill Dean’s request. He let his hand fly to his dick, pumping with more ferocity than he’d ever before because _holy shit Dean was fucking him. He had Dean’s cock in his ass and it felt so fucking amazing and oh god he was going to come on his friend’s dick._

Then he was done for. His whole being exploded with that orgasm but he didn’t have time to relish in the way Dean looked as Cas came on his cock because before he knew it Dean’s face was buried in his neck and his friend’s hips were pistoning into him at an unreal speed. 

“Fuck—I’m coming. I—uhhh.” That last thrust, just before Dean pulled out of him, had Cas’s toes curling. Before he could even think to pull Dean close, his friend had already pulled out and was spilling his release across Cas’s stomach. 

He didn’t so much as think but react when he pulled Dean down atop him, feeling comforted by the weight of his friend as they regulated their breathing. Cas didn’t realize his fingers were coursing through Dean’s sweaty hair until his friend pulled back, just slightly and looked him in the eyes. Naturally, there was doubt in Dean’s gaze. 

“Are you okay?” He asked, smoothing back Cas’s hair subconsciously. 

“Yes.” 

Castiel could feel Dean’s chest shaky against his own. “Was… was that good for you?” 

“Yes.” 

He knew his single syllable answers had Dean worried but he didn’t feel capable of saying much else. 

“Cas?” 

“I’m okay.” He choked out, finally. “I’m good. That was…” 

“You were amazing.” 

Castiel knew his face probably looked pathetically pleading but he hoped to God, Dean was telling the truth. 

“I was?” 

“Yeah.” 

A timid smile crossed his face. “You were too.” Cas insisted. “Thank you.” 

There was something in the look that Dean gave him that Castiel couldn’t decipher but too soon Dean pulled away, insisting on cleaning them up. Before he could even count to twenty Castiel was pulled tightly into Dean’s arms, more securely than he’d ever been before. 

He sighed into the embrace and tried not to let his mind cloud with the enormity of what had just transpired between them. It changed things. It changed everything that was between them but Castiel could not find it anywhere in him to regret it, even for a moment. He’d just given a part of himself to the one person he’d longed to give it to and here he was lying in that person’s arms feeling almost… cared for.

He wanted more than anything to ask what was going through Dean’s mind but knew his friend needed to be in his own headspace to process this all so Cas let him be knowing neither of them were likely to fall asleep anytime soon. 

After what could have been an hour or five minutes Dean squeezed his arms around Cas tighter and finally spoke. 

“I just… I just need you to know I don’t—I won’t ever take that for granted.” 

“I know.” Castiel replied easily, not needing to look into Dean’s eyes to see the truth. He couldn’t be happier that Dean was the one with him right now. 

“Thank you.” His friend whispered then too. 

Castiel wasn’t sure what the thank you was for but it made something in his core loosen just a bit. This had really happened. This was a moment he’d carry with him forever. For the rest of the night he just let himself be held. 

It was everything he’d ever wanted.

**Notes for the Chapter:**

> I'm going to go hide for a while now. Lines were definitely crossed but I do hope you all like where I take this. There will be angst, but honestly, not for a while despite how it may look.


	10. November 13, 2017

Mon, Nov 13, 2017 1:05

**Cas:** Are you home? 

_Dean:_ Yeah? 

**Cas:** I forgot my laptop charger and I’m at 7%

_Dean:_ I’ll meet you with it. 

Mon, Nov 13, 2017 1:42 

**Cas:** Thanks for bringing it to me. 

_Dean:_ No problem

Mon, Nov 13, 2017 2:07 

**Cas:** I’m so bored. I just want to go home. 

_Dean:_ You really shouldn’t be texting in class. Such a slacker. 

**Cas:** Hypocrite. I don’t think you’ve ever taken any notes in your life. At least I can multitask. 

_Dean:_ Yeah, yeah, yeah, you’re the brains 

**Cas:** I’m glad you can admit that 

_Dean:_ So… when you get home, do you wanna…? 

**Cas:** Yes

Tues, Nov 14, 2017 5:34

_Dean:_ Do you want Chinese for dinner? 

**Cas:** That sounds wonderful. 

**Cas:** Pork fried rice this time. Not chicken. 

**Cas:** And crab wontons. 

**Cas:** Thank you, Dean 

_Dean:_ No problem 

Thurs, Nov 16, 2017 6:09 

**Cas:** [Attachment: 1 Photo]

_Dean:_ Holy fuck Cas! Benny almost saw that!! 

**Cas:** Should I not have sent it? 

**Cas:** I’m sorry.

**Cas:** I just thought I’d try it out and I thought sending a picture might be something to try out too... I’m so sorry. I really didn’t mean to embarrass you. 

_Dean:_ Hey stop. 

_Dean:_ It’s cool! 

_Dean:_ I liked it! I swear. 

_Dean:_ I just wasn’t expecting it and opened it without thinking. I thought it was just a random gif of some funny shit. I didn’t expect it to be that. 

_Dean:_ But I liked it! I promise! 

_Dean:_ Does it feel good? 

**Cas:** It’s interesting. I don’t really feel it unless I move. 

_Dean:_ Keep it in

_Dean:_ Until I get home 

**Cas:** Okay 

Fri, Nov 17, 2017 7:25

_Dean:_ Did you take my Zepp shirt? 

**Cas:** I’m sorry. I’m wearing it…

_Dean:_ It’s cool 

**Cas:** I haven’t done laundry yet and it was the first thing I saw. 

_Dean:_ Not a big deal. 

_Dean:_ And no surprise there 

**Cas:** Hannah says hi 

_Dean:_ Tell her I’m still mad at her for forgetting my cherry pie 

**Cas:** She says you don’t deserve it and that she’s making one all for me and I can’t share. 

_Dean:_ You’d betray me like that? 

**Cas:** You’ve had her pie 

_Dean:_ You have a point 

**Cas:** Are you going out tonight? 

_Dean:_ Yeah Ash says he wants to get hammered 

**Cas:** Be safe 

_Dean:_ You too 

**Cas:** Call me if you need a ride home

* * *

Dean was kind of living the dream. 

Not only did he get to see Cas’s naked body more than he ever had before but he now had the added benefit of being able to press his own naked body up against it. And holy fuck was he pressing his body against Cas’s every chance he got. It felt like they were back at the beginning of their arrangement with how eager Cas was to try everything he could. And by god, Cas was probably part rabbit because _holy shit_ Dean’s dick had never had so much action in his life and it’d only been a week. 

Cas was insatiable right now and Dean was so down for that ride. 

With how much sex they were already having he almost didn’t have time to linger on the fact that he was probably the scummiest scumbag to ever walk the face of the planet, but oh was it there, settling in the back of his mind. 

He’d been too weak willed. He’d wanted Cas so badly, and for too long, that Cas didn’t so much as break his will as he just dusted it away. And fuck, it’d been amazing. It’d been everything he’d been fantasizing about but so much more. It… it _meant_ so much more than anything he’d ever done before and not just because it was Cas’s first time but because it was Dean’s first time with someone he really, truly, cared for. 

He cared that Cas trusted him that much. He cared to make it as good for his friend as possible. He cared about Cas’s feelings and wanted to ensure that he felt safe in his decision to give that part of himself to Dean. He cared so fucking much he didn’t know what to do with himself. What he did know was now that the dam had been broken, he couldn’t stop himself from having as much of Cas as he could get. 

And right now he had his hands all over Cas’s skin, trailing up over the back of his thighs. It was perfect, it was all just so fucking perfect he felt like he was going out of his mind. The plains of Cas’s stomach were smooth and trembled just slightly every time let his hands wander just enough to caress. His thighs and his legs, rough with hair—something Dean never once thought he’d find sexy but knowing that _he_ got Cas made everything about what they did feel like heaven. Even the path of his smooth back made Dean’s mouth water. What was it about his best friend that made him lose his mind? 

He wasn’t going to question it. If he thought it over too much he’d realize that he had no right to touch something so good; he didn’t deserve this. He didn’t deserve Cas. 

But he did it anyway and he tried to make it as good as possible. If at all possible, in the future, Dean wanted Cas to be able to look back at his first sexual experience and remember it fondly. He didn’t want Cas to remember him as ‘just some guy I fooled around with,’ he wanted Cas to remember him as someone who actually took care of Cas’s needs and didn’t just take it all for himself. 

He knew in some ass backwards way _he_ was the one who’d gotten too attached over Cas losing his virginity but it wasn’t like he could go back now. And Lord, help him he didn’t want to. 

“Dean please.” 

A smile pulled at Dean’s lips; not that Cas could see though, as his face was smashed into the pillows just waiting for Dean to get on with it. He wouldn’t admit it aloud but his simple caressing of Cas’s skin may have turned into a gentle massage just because Dean couldn’t resist those sighs of comfort. 

“Oh? Did you need something?” Dean asked, trailing his fingers over each of Cas’s ass cheeks, willing his friend to ask for what he wanted.

“You’re an assbutt.” 

“An assbutt? I see how it is. Too bad. I thought you might’ve liked what I was planning.” 

“_Dean!_” It was the whiny quality in Cas’s voice that had Dean’s eyes fluttering shut as he tried to keep his dick from taking complete control of this situation. 

As much as he liked getting to have sex all day every day, (not literally, though he’d be up for it if Cas ever asked) he and Cas still had an arrangement, and Dean was trying to hold up his end of the bargain. 

The morning after they’d crossed the line, Dean could hardly focus on the fact that he’d gotten to sleep with Cas in his arms. Instead his stomach churned with nervousness that Cas would regret what they’d done and want nothing more to do with Dean. He didn’t know what he would do if everything ended right there for them, so, he waited, watching his friend sleep for nearly an hour an hour more. 

Cas had looked nearly angelic as he woke up and stretched, burrowing his face into Dean’s collarbone in the fight to get just a second more sleep. When his friend finally did force himself awake, nothing felt different. Cas didn’t even look at Dean differently. He just smiled and asked if they should go get breakfast and Dean’s heart nearly tumbled out of his chest. 

He’d honestly worked himself up to believe that with a night to sleep on it, Cas would have realized he wanted nothing more to do with Dean and there was nothing left for them to explore. Dean didn’t want to put too much thought into why it made him feel like a weight was pressing in on his chest at the thought of not getting to touch his friend ever again but it was there and it felt like hell. 

Even later on that night, when they were alone in their dorm room Dean was fairly certain Cas was going to end it all. They’d reached their end goal hadn’t they? Cas wanted to learn how to have sex and be what his partner would want in bed and… well if Dean had to say so himself, Cas was fucking incredible. Anyone who ever got to be with Cas would be a damn lucky son of a bitch. 

Dean’s mind was too frazzled to really pay attention to what Cas had been stammering later that night. He hardly registered many words, too caught up in his thoughts of _‘This is it. Fuck this is really it.’_ but somehow a few words had managed to slip through. 

When Cas had said, _“I’m just not certain I’m ready to end our arrangement, there’s still so much I don’t know.”_ Dean didn’t know if he was able to contain the sheer elation he was feeling. He’s not sure he even let Cas finish his sentence before Dean was agreeing to do anything Cas wanted to try. 

That’s how they were here, with Dean resisting temptation, waiting for Castiel to use his words and ask for what he wanted because Cas had said he wanted to not be so shy anymore. They’d only been sleeping together for a week, so Dean didn’t expect his friend to ooze confidence, but Cas had asked for this and Dean knew he’d do anything for the other man. 

“What do you need?” Dean asked with a playful voice, still trailing his fingers any which way. 

Cas buried his face deeper in the pillow and growled, obviously frustrated with his shyness. It made Dean laugh to himself. 

“Touch me you dick,” Cas mumbled. 

“I’m a dick? Or you want me to touch you with my dick?” 

“I hate you.” 

“Are you sure about that?” Dean pressed his pelvis forward just enough to line his dick up with the crease of Cas’s ass. 

“Please.” 

“Please what?” 

“Dean…” 

“You tell me what you want and I’ll give it to you.”

There was a moment of silence as Cas seemed to try and reign in the strength he needed to voice what he wanted. His voice was low and soft when he finally managed to find it. 

“Please have sex with me again.” 

Dean’s face broke into a stupid grin and he tried to hide his chuckle at that phrasing, not quite as explicit as Cas had been their first time but it still did the trick. 

A part of him was still certain that he was a piece of shit for allowing himself to have this with Cas but the alternative was watching Cas have this with someone else and that… that was something Dean didn’t think he could do just yet. He needed more time. Just a little more time and he’d get over whatever it was he was feeling. It was just too new. Like the honeymoon stage but for friends with benefits. 

He shook the thoughts out of his mind. He’d deal with them later. Right now Cas needed his attention and he wasn’t going to disappoint. Especially since his friend had asked so nicely. 

With one delicious movement of his hips he pressed himself into Cas’s tight heat.

* * *

Mon, Nov 20, 2017 3:28 

_Dean:_ Sammy just said he’s coming for a week. He gets in tomorrow night but I thought he was supposed to get here Wednesday. Can you pick up a little before I get home? I’ll help when I get back I just don’t want him to find anything… 

**Cas:** Of course. I’ll make arrangements to stay somewhere else too. 

_Dean:_ No.

_Dean:_ I mean if you want to you can. But you can stay too. 

**Cas:** Well you can’t make your brother sleep on the futon. Not only is it uncomfortable as a bed but with what we’ve done on it… I’m not sure if I’m comfortable letting Sam sleep there. 

_Dean:_ You have a point. I can sleep on the futon though. 

**Cas:** It’s okay. I don’t want to intrude on your time with your brother. I’ll stay at Hannah’s. I believe her roommate will be out for the majority of the weekend. 

**Cas:** McDonalds? 

_Dean:_ You wouldn’t be intruding. 

_Dean:_ Yes please. Double quarter pounder 

**Cas:** Fries? 

_Dean:_ Duh 

_Dean:_ Really you can stay with me and Sam. 

**Cas:** I’ll see you at home. 

Tue, Nov 21, 2017 6:22

_Dean:_ He said his plane just landed 

**Cas:** Tell him I say hi

_Dean:_ Will you stay at home until we get back? He’ll want to see you

**Cas:** If you’d like me to

_Dean:_ Yeah

**Cas:** I’ll be here 

Wed, Nov 22, 2017 1:58

_Dean:_ Sam’s not bugging you right? 

**Cas:** No he’s being quite pleasant. Telling me about how you used to wear Hannah Montana shirts to school every day. 

_Dean:_ Okay fuck you that never happened. 

**Cas:** No, I guess not. But you apparently had very blonde hair and parted it down the middle going by the pictures he’s shown me of you in high school. 

_Dean:_ I was still hot as hell. 

**Cas:** …. 

_Dean:_ Fuck you. 

**Cas:** Please? 

_Dean:_ I wish… He’s leaving in a few days. 

Thurs, Nov 23, 2017 11:41

_Dean:_ Dude Sammys snoring so fuckin’ loud

_Dean:_ I blame it on the turkey 

**Cas:** It was delicious 

_Dean:_ How’s Hannah’s floor?

**Cas:** I’ve slept better. 

_Dean:_ Sorry for kicking you out. I thought you said her roommate was going to be gone.

**Cas:** You did no such thing. I offered to stay here. 

**Cas:** Apparently she had an argument with her family and didn’t want to go back. It’s no big deal. I’ve slept here before. 

_Dean:_ Ya. I know. Still feel bad. 

**Cas:** You’ll just have to make it up to me. 

_Dean:_ What do you have in mind? 

**Cas:** I’ve been interested in trying out different positions. I’m fairly flexible so I’d like to see if they’d work. 

_Dean:_ Fuck. Can I kick my brother out? 

**Cas:** I wish… 

_Dean:_ Shit. Me too. We should probably go to sleep though. Nothing worse than blue balling ourselves and I can’t exactly get off with my brother in the same room. 

**Cas:** Good point. 

**Cas:** Goodnight Dean

_Dean:_ Night Cas 

Fri, Nov 24, 2017 3:03

**Cas:** I’m going to stop by and pick up my chargers. 

_Dean:_ You don’t need to ask it’s your place too 

**Cas:** I don’t want to impose on your time with Sam.

_Dean:_ Dude you’re not imposing 

_Dean:_ He’s been asking about where you’ve been 

**Cas:** I didn’t want to make anything weird 

_Dean:_ Nothing is weird

_Dean:_ Do you think things are weird? 

**Cas:** Of course not. I’m happy with our arrangement. 

_Dean:_ Then stop hiding. Sam misses you. 

_Dean:_ I miss you 

Sat, Nov 25, 2017 1:13

_Dean:_ You didn’t tell me that the turkey club had lettuce onions and tomatoes on it! 

**Cas:** Vegetables won’t kill you, Dean. 

_Dean:_ Tell that to my corpse. 

**Cas:** Such drama. 

_Dean:_ my ass! 

**Cas:** What about your ass?

**Cas:** It is a nice ass 

_Dean:_ You check out my ass, Cas? 

**Cas:** On occasion. 

_ Dean:_ Like what you see? 

**Cas:** I’ve seen better. 

**Cas:** That’s a lie. 

_Dean:_ Thinking about my ass right now? 

**Cas:** Maybe. 

_Dean:_ ;) 

_Dean:_ Might be thinking of yours too 

“What are you laughing at?” 

Dean looked up from where he’d been holding the phone under the café table. He nearly dropped it like a kid caught red handed. 

“N-nothing!” He sputtered quickly, earning himself a look of incredulity from his brother. He’d been getting that look a lot the past few days and he didn’t like the way they made him feel. 

“You’re lying.” 

“N-no I’m not. I’m not lying.” 

He swore it’d only been a few months since he’d seen his kid brother but the friggin’ bean sprout had somehow shot up about five inches and was now sporting some awkwardly patchy facial hair that made him look fractionally older than seventeen. The brat even had that teenaged know-it-all attitude that had been grinding on Dean’s nerves every so often.

“Dean, you’re acting weird.” Sam exclaimed, making Dean scoff under his breath. 

“No? I’m cool.” 

“You’re shifty. Like you think I’m going to find out you stole another one of Bobby’s cars to go hook up with your girlfriend.” 

“No. Nope. I’m all good.” 

“I know when you’re lying. What’s going on?” 

He knew his brother was right. He knew he’d been acting weird since Sam got here but Dean didn’t know how else to act. He was trying to pretend like he wasn’t sleeping with his best friend even though Sam would not shut the fuck up with his constant ‘Who are you seeing Dean?,’ he was trying to pretend like he didn’t miss the hell out of his best friend because this was the longest they’d been apart in months, and he was trying to pretend like he wasn’t horny as hell because he’d _just_ gotten used to having Cas any chance he could have him and he hadn’t quite gotten his fill yet. 

His brother wasn’t an idiot. Of course he knew something was up with Dean, but that didn’t mean Dean was just going to spill his guts to the kid. 

Thankfully his phone distracted him from answering the question at hand. 

Sat, Nov 25, 2017 1:32

**Cas:** I’m nearby. Can I join you and Sam?

_Dean:_ Yeah! 

“Cas is going to meet us. That okay with you?” He asked Sam in lieu of answering the question. 

“Course it is.” 

That was all Dean needed to distract his brother from bringing up why Dean had been acting weird. He managed to eat most of his sandwich too while they waited for Cas to get there. Dean went ahead and grabbed his friend an iced mocha and turkey club to have when he met up with them, knowing that they had little food in their room and Cas probably hadn’t bothered making anything. 

Sam might have given him a weird look for it but Dean didn’t really care. A hungry Cas was a grumpy Cas and Sam could just shut his giant mouth. 

“Hello, Dean. Sam.” Cas said respectfully as he approached the table. He was wearing jeans and one of Dean’s t-shirts again (which did not, at all, make a thrill run through Dean) with his signature trench coat overtop, the damn thing finally making it out of hibernation. 

Sammy moved to push out a chair for their friend. “Hey Cas!” 

“How has your day been going?” 

“It’s been good. What about yours? Haven’t seen you much.” 

“Here, I ordered for you.” Dean cut in before Cas could answer, sliding the plate in front of him.

It was well worth the odd looks his brother had been sending him to see how Cas’s face lit up at the sight of food. “You didn’t have to do that. Thank you.” 

“No biggie.” Dean shrugged, fighting off a satisfied smirk. 

“To answer your question Sam,” Cas said turning back to the overgrown weed, “it’s been mostly well. Had to recover from a bit of a hangover this morning however.” 

Dean gave his friend a sympathetic wince. “Did you and Hannah go out last night?”

“Oh yes. It was a good time.” 

“Where’d you go?” 

“We started at Piranha but ended up at Marquee. I believe there were a few stops in between.” 

“Was it her idea to start there?” 

“It always is. I believe it’s her hope that I’ll find my one true love.” 

Sam and Dean both laughed together. Dean knew it was something Hannah would do. She seemed to believe in true love and happily ever after, and always tried to encourage Cas to go out and meet someone good for him. 

“Did her dreams come true then,” Sam asked. “You meet anyone?” 

Just hearing Sam ask that made Dean clench up. The thought of Cas meeting anyone else hadn’t really crossed his mind but knowing it was a possibility was terrifying. 

“No. Of course I didn’t meet anyone.” Cas replied dismissively, as if it were unheard of for people to meet at a club and hit it off. Dean didn’t understand. He knew that they owned a mirror, Cas couldn’t be that blind, could he? 

“I don’t believe that.” Sam said to Cas, earning himself a sideways look from the blue-eyed boy. 

“I kind of don’t believe it either.” Dean piped in. “Hannah says you always get hit on when you two go out.” 

Dean was, not at all, not even a little, not one smidge jealous of that. Cas was an attractive guy. People liked to hit on attractive people. It was normal. He didn’t care. Everyone could hit on Cas if they wanted to. It didn’t matter to him. 

Only that it did and he hated that he was bothered by it. 

But he was an asshole for letting it bother him. 

His best friend _should_ be getting hit on. His best friend _should_ feel wanted and attractive. His best friend _should_ have other people who aren’t complete dipshits like Dean to be with… 

Dean tried to not let his thoughts show in his features as Cas added to the conversation. 

“Well there were a few people who approached me but I was having more fun with Hannah. Besides they—they don’t mean it.” 

“What do you mean?” Sam asked. 

“They don’t actually find me attractive. They’re just the type of people who hit on everyone.” Cas seemed so nonchalant in his delivery that Dean feared the guy actually meant it.

“Dude, what? That’s not true.” 

Dean stared his friend down, wondering where in the hell he got the idea that people didn’t find him attractive. Cas seemed unshakeable in his belief, rolling his eyes at Dean’s words. 

“Regardless, it was a fun time.” Before Dean could argue any further Cas changed the subject. “Oh Dean, you know what was weird? We bumped into Benny at one point on the street and he and Hannah were actually talking.” 

“No shit? Did he finally grow a pair?” 

“No, I don’t believe so. She would have told me.” 

“Yeah, you’re probably right.” 

This conversation seemed to come as a shock to the out-of-towner. “Wait? Benny likes Hannah?” Sam asked, sounding blown away by this bit of news. 

“Dudes been pining for years.” 

“But he hasn’t asked her out?” 

Dean almost wanted to laugh at his brother for his high school ideals about love. 

“He’s just a giant chicken shit,” he said instead of teasing his brother. Sam seemed appalled by Dean’s answer nonetheless. 

“He should just ask her out if he likes her.” 

“It’s not that simple kid. Besides, Hannah doesn’t like him like that.” 

Next to him, Cas made a sound of argument around the sandwich he was munching on. “I’m not certain that’s true. She’s never said explicitly which way she feels.” 

“Still, he shouldn’t risk asking her out if he isn’t sure she feels the same.” 

“I think she might be waiting for him to make the gesture. To reassure her that he is serious.” 

“The dude is so into her, everyone can tell.” 

“Everyone except her, perhaps.” 

Dean and Cas shared a look of mutual disbelieve in their friends’ antics—their two friends circling around each other but clearly not willing to make the first move. If only those two could get their acts together then everyone else around them could suffer a little less. 

Sam, however, didn’t seem to care about the topic at hand anymore and switched it quite suddenly to something he’d been dying to know for the past few days. “So, Cas, is Dean seeing anyone?” 

“Excuse me?” Cas sputtered suddenly. Dean glared at his brother. 

“Sam, will you stop already?” 

“What? You won’t tell me anything! I keep asking but you keep saying that you’ve only been with one person in the last six months. I don’t buy it. So what’s the truth Cas? You’d know better than anyone.” 

Dean closed his eyes to try and keep himself from punching his brother in the face. He’d been trying so hard to steer clear of this specific topic and had even resorted to telling his brother a partial truth to keep him from knowing the real truth! He knew how it probably looked though. Dean Winchester only sleeping with one person in a six-month timespan? To his brother that probably seemed like a blatant lie. 

It was Dean’s fault Sam thought it though. _Maybe_ Dean had inflated his stories to the kid a few too many times and had insinuated that he’d been with more than double the number of girls he’d actually been with. At the time he’d wanted his brother to think he was cool but he’d clearly failed miserably at it since all Sam saw him as was a giant man slut who couldn’t just stick with one person for an extended period of time. 

The only silver lining Dean saw with Sam bringing this us was that Cas knew firsthand that Dean wasn’t, in fact, slutting it up. He looked to his best friend to see Cas with a much paler complexion, looking like he’d rather be anywhere else. Dean pleaded with his eyes for his friend to back him up and only that seemed to shake Cas out of his stupor. 

“He’s telling the truth. Unless he’s been sneaking around and I’m not noticing.” 

Dean turned smugly to his brother. “See? What did I tell you?” 

“Wait. So you’ve been dating one girl for six months and only sleeping with her? Or you’ve gone completely celibate in the past six months?” 

Fuck. Fuck fuck, fucking fuck. He didn’t want to lie to his brother but he also knew he couldn’t tell the truth either. And for whatever reason the thought of saying he was dating some random girl didn’t sit well with him. Besides, Sam would nag him all weekend to meet her if Dean did lie about it. He didn’t know how to answer, which is why what he said came out sounding more like a question. 

“Uh—the second one?” 

“You’re a liar! I know when you’re lying. Cas, back me up!” 

Cas looked like he’d been caught with his hand in the cookie jar. It was almost comical how wide his eyes had gotten and how rosy his cheeks flushed. Dean tried to make eye contact with his friend to reassure him that it was okay to lie to Sam about this, just for the moment, but Cas was already fishing around in his trench coat pocket. 

“I—I uh… oh! Look. Hannah is calling. I need to—I will see you both later? Okay? Bye.” 

Dean tried to reach out and grab him by the arm but Cas was too quick. Dean didn’t know what the hell just happened. 

Apparently neither did Sam. “What the fuck?” 

Did Cas hate lying this much too? Did it upset him that Sam was asking these questions? Did Cas think Dean was going out and sleeping with other people? Surely he’d know that Dean would never do that to him? Fuck. Dean didn’t even have the slightest urge to seek out anyone else. He was completely satisfied. It was probably the lying that was eating his friend up, and truth be told, it was kind of eating Dean up too. 

The amount of times that he had to lie to Benny or Ash telling them that he “just wasn’t in the mood for hooking up” anymore when he really wanted to say “I’m having the best sex of my life with Cas,” was starting to get to him. Having to turn down nights out with friends with a flimsy excuse of “I already have plans” instead of saying “I have plans with Cas” just so no one would grow suspicious of the amount of time Cas and Dean _weren’t_ leaving their room… that too was starting to get to him. 

“Dean?” Sam asked, still looking in the direction Cas had run off in. “What the fuck just happened? What’s going on?” 

Now being here with his brother, the one person who had been by Dean’s side all of his life, the kid he’d give his life for in a heartbeat—having to lie to him about something that was making Dean so damn happy, it didn’t sit right. 

What was he lying for anyway? 

He knew he and Cas agreed to not tell anyone but this was Sam. If anyone would understand it would be his brother. 

And the kid loved Cas anyway. 

Knowing that, and knowing that it was pointless to keep trying to give his brother run around answers all weekend, had Dean word vomiting: “I’m having sex with Cas...” 

Sam’s eyes blew wide. “Whoa. Holy shit. What? How did you not care to mention this like _four days ago_?” 

Dean’s heart was suddenly pounding in his chest at an unreal speed but he tried to play it cool. 

“It’s not that big of a deal.” 

“Not a big deal? That’s a huge fucking deal. You and Cas are a thing? I didn’t really picture that happening but… I mean, I can see it—“ 

Suddenly Dean felt like he’d put his foot in his mouth. Sam thought they were a thing? Like a _couple_ type thing?

“Whoa, whoa, whoa. It’s not like that. It’s just... he just.... he wanted experience.” 

“What does that even mean?” 

Dean floundered for an answer. How exactly was he going to explain this to his brother? Should he even try to explain the entire situation? It could go either way really. Dean, opted for honesty, deciding he couldn’t go back now. 

“He’d—Cas, uh—he’d never done anything before and he... he asked me to help him.” 

Sam nodded in seeming understanding but seemed less thrilled than he’d been moments ago. “So you’re just friend’s with benefits?” 

Was that what they were? Friends with benefits? They were friends and it was mutually beneficial getting to have all the orgasms they could hope for but… Dean had seen that movie (and all the ones that came out in the exact year with extremely similar plot lines) and he knew that one common theme was that both parties were both hiding real feelings during the whole ordeal. 

But with him and Cas, that just wasn’t the case. 

On his side, yeah, there was something going on, especially when he got to hold Cas close but Cas? No, that guy wasn’t dumb enough to feel anything for Dean. This whole situation was strictly a learning experience to his friend. Cas hadn’t even ever asked to kiss while they were messing around. And isn’t that what people who felt things for the person they were sleeping with did? 

But that still didn’t answer the question: what were they? 

He didn’t love the label but it seemed to fit better than ‘Roommates Who Have Sex” because, really, they were much more than roommates. ‘Best Friends Who Fuck… Often” didn’t sound right either. 

“I guess?” Dean answered his brother, feeling heat creep up the base of his neck. 

“What do you mean? You’re having sex, right?” 

“Well yeah? I just said that…” 

“But are you dating him?” 

“No. No. No, we aren’t dating.”

“Okay? So you’re just hooking up and that’s that?” 

“Yeah.” 

Dean could barely look at his brother but he knew by the tone that Sam’s face had morphed into that of judgment. “How long has this been going on?” 

“Uh… like th-three months?” 

“But you said you haven’t slept with anyone in six months?” 

“I haven’t… Honest. No one except Cas. I was—I was in a bit of a dry spell.” 

He didn’t know why he felt an awful lot like a scolded child who’d just been caught painting on the walls. Hell, he probably hadn’t even been scolded since he was in high school and Bobby caught him and Cassie Robinson in the backseat of one of the junky cars at his shop. 

“Then what? How did this even happen? You got too horny and jumped your best friend?”

Dean really didn’t like his brother’s tone and felt himself get defensive. “I told you, he asked for experience and I agreed to help him out.” 

“How chivalrous of you.” The condescending tone was hard to miss but Dean ignored it. “So you’re just doing Cas whenever you feel like it? Out of friendship?” 

“More he’s doing me.” 

“What?” 

Dean looked up at his brother with a questioning look before he realized what exactly came out of his mouth. He rushed to clarify. 

“No—wait that came out wrong. I don’t... I don’t do things to him. I mean like I touch him and I do things to him and uh, he doesn’t do all the work... I just don’t… I don’t touch his dick or like kiss him or anything…”

There was a long, very poignant pause between them. Dean’s eyes stayed on his brother’s face, wondering what the hell Sam was thinking. By the looks of it, Sam wasn’t thinking anything positive. 

“You’re being serious? You just—you don’t even—” When Dean’s face clearly didn’t show what Sam had been hoping it would the look of shock turned to anger. “What the fuck Dean? Why does it sound like you’re using him? Is this all just _convenient_ for you?” 

“No! Hell no. I’d never do that.” 

“But you just said you don’t even touch him or kiss him? How does that even work? You just fuck him and then go back to playing video games? I don’t get it.” 

Dean barely remembered to keep his voice from shouting at his brother, they were still out in public with anyone able to hear this conversation. He lowered his voice to growl and gave his brother a stern look. How dare Sam think that he’d be capable of using Cas like this? Didn’t Sam know him better than this? 

“You don’t understand! We have an agreement! He—he was a virgin. Some asshole said they didn’t want to sleep with a virgin and Cas asked me to help. He just wanted to learn how to be confident and learn more stuff in bed and that’s what I’m doing. I’m helping him. I’m teaching him. We don’t need to kiss or anything for me to help it. It’s working for us.” 

“Right.” 

“What’s your fucking problem?” 

“I don’t know if I believe you right now. This is coming from the mouth of the man who bragged for years about hooking up with twins because he was ‘just that irresistible’. The same guy who told me he was spending his freshman year ‘single handedly working through the Alpha Phi sorority.’ You want me to believe you’re not just using your best friend because he was the simplest way to get your dick into something daily?” 

Dean felt a little like someone had just bitch slapped him. 

That’s how his brother saw him? 

That’s… that’s the reputation he had in his brother’s eyes? 

Those were just stories he told his brother as a joke to make himself look cool. 

He wasn’t… he wasn’t that type of guy. He just wasn’t. 

Yeah maybe he slept around a little but not like an _obscene_ amount. Less than ten girls ever, honestly. Mostly he just fooled around with them in his car and got a little handsy but all the way? That wasn’t his style. He just… he just boasted a little more than was necessary because he thought… he thought it would make him look better. Cooler.

He could see how he’d fucked up. It was evident in the mild disgust Sam held in his features. 

Surely his brother had to know that it was all just bullshit the way Dean used to brag. He wasn’t a complete dickwad. Maybe he didn’t stick around for the morning after and maybe he didn’t remember their freaking majors or anything but he remembered all of their names. He didn’t just use people and discard them like his brother seemed to think. 

“Sam,” Dean went to start but Sam cut him off quickly. 

“You know what I’m wondering? What are you going to do when this ends up biting you in the ass and you lose the only real friend you’ve ever had?”

“Don’t say that—” Dean’s voice wavered a little. “This… this is working between us and we’re still best friends. Nothing is going to change that.” 

“Funny. I don’t fuck my best friends. Especially my dude friends when I’m ‘apparently’ straight.” 

What Dean didn’t expect from this conversation was to end up with his brother angry with him. Dean especially didn’t expect to realize that his brother thought so lowly of him either. It actually fucking hurt. 

Emotion was constricting his throat a little. He just wanted to go back to his room. “You know what? I really thought I could tell you this. I really thought you’d understand. Guess I was wrong. I’m—I’m gonna go.” 

“Dean... wait.” Sam huffed, attempting to stop Dean from standing up, but Dean pulled away too quickly. 

“No! You don’t understand. I’m not some scumbag like you think I am. I’m not using him to get my rocks off. I’d never do that!” 

“Okay maybe you aren’t but you have to admit the way it looks seems…” 

“I’m not using him.”

Sam closed his eyes and took a deep breath, obviously trying to not yell at his older brother. The look he gave Dean when his eyes did open was a mix of exasperation and pity. It made Dean’s shoulders tense. 

“It’s just—you said it yourself, you’re a ‘one and done’ kind of guy. But now you’ve been hooking up with your best friend as some sort of learning experience for him and you want me to believe that? You want me to believe that you are doing this out of the goodness of your heart and not because you’re just thinking with your dick? It’s weird, Dean.” 

“Sammy…” 

With that his brother rose to his feel and shook his head, looking extremely disappointed. “I’m gonna take a walk around the campus. I don’t really want you to go with me.” 

Sat, Nov 25, 2017 5:40

**Sam:** I’m at Benny’s. Going to stay here tonight. 

Dean stared at the phone wondering how he’d fucked up so badly that the one time he got to see his brother in months, he managed to drive the kid away. 

Sat, Nov 25, 2017 5:46

_Dean:_ Just come back so we can talk. 

**Sam:** I’d rather play video games here. 

**Sam:** I don’t really want to talk to you about this. I haven’t changed my mind. 

**Sam:** I just think Cas deserves better. 

**Sam:** You should end it before he gets hurt. 

_Dean:_ Sammy please

He waited ten minutes for his brother to reply before he sent off a text to Benny telling him if they let the kid drink or smoke he’d disembowel them immediately before he shot off a text to Cas. 

Sat, Nov 25, 2017 6:02

_Dean:_ Sammy’s staying at Benny’s tonight. You can come back if you don’t want to sleep on the floor. 

**Cas:** I’ll be right over 

Dean didn’t really know what he was doing. He didn’t want to talk about Sam being upset with him but he also didn’t want to be alone. He definitely didn’t want to talk to Cas about _why_ Sam was mad at him…. No. They’d agreed that they weren’t going to tell anyone and Dean went and broke that rule. Not that Cas would be mad at him for it… but if Cas knew that Sam knew then it’d all feel real and Dean was steadfastly ignoring that feeling as hard as he could. 

Despite knowing that Cas would know something was wrong with him immediately, Dean didn’t want his friend sleeping on the damn floor of Hannah’s dorm room when they had perfectly good beds to sleep on in their own, so he planned to distract his friend by any means possible if the topic of Sam came up. 

When Cas let himself into their home and dropped his stuff, it was almost instant that he picked up on Dean’s dreary mood.

“Are you okay?” Cas asked as he fell into his beanbag with a groan. Dean watched his friend twist his torso left and right trying to get a satisfying crack out of it. He felt like a dick for making his friend sleep on someone else’s floor. 

“Yeah, I’m cool. Just tired.” Dean deflected, still not wanting to speak of his and Sam’s tiff. 

“Did Sam tire you out?” 

“Kind of.” 

“Why’s he at Benny’s?” 

Dean could see it in his friend’s eyes that Cas knew something was off with the whole situation but Dean knew better than to fall into that trap. That’s where unacknowledged feelings laid and Dean was still allergic to those currently. 

He shrugged and gave his lie of an answer, “He probably got talked into a gaming match. I didn’t really ask.” 

“Oh? You didn’t want to join them?” 

Not that Dean would have been invited, but Cas didn’t have to know that. Besides, he didn’t really want to spend a night playing video games with those guys. What he did want was a normal night in with his best friend who he’d barely gotten to see in the past few days. 

“I thought we could hang out. Haven’t really seen you this week.” 

“What do you have in mind?” 

With Cup Noodles in their hands and the TV remaining off, they spent the next hour or so talking about random day-to-day shit that came to mind. Dean gave his review of the vegan chocolate cake Hannah had made for Thanksgiving, which brought their train of thought to turkey sandwiches then to turkey clubs and how Dean felt about the one from earlier. Which led to:

“Oh! Yeah? What was up with your disappearing act today?” 

Cas slapped his own forehead and groaned, clearly embarrassed by his behavior. “God… I’m sorry. I felt like such an idiot after I left. I just got flustered. I didn’t know what to say.” 

“It’s cool.” Dean laughed off. Realizing that he’d just brought them too close to dangerous territory. 

“Did Sam think it was weird? What did you even end up telling him?” 

“He—he didn’t notice.” He lied smoothly, “And uh—I just… I just told him I was trying to become the next Pope. I think he bought it.”

“Right… you as Pope.” Cas added an overly dramatic grimace. 

“You don’t think I can be Pope? I’m holier than thou.” 

His friend tried to battle away a smile as he straight-faced his response, “You are so right. I guess this means we must end our arrangement in order to you to follow your true path in life.” 

It was the glint in Cas’s eyes that had Dean lowering his voice suggestively. “I won’t tell if you don’t tell.” 

Cas smirked. “I do believe lying is a sin.” 

“Damn.” Dean huffed out in joking anger causing both of them to laugh. It’d hardly been two hours and Dean was already feeling lighter, just from having his friend with him. He couldn’t stop smiling as he looked over at Cas. “I feel like we haven’t been alone together in weeks.” 

“I know. I feel like that too.” 

“It’s weird just seeing you in passing and not spending the afternoon with you.” That was an understatement if he were being honest. It threw off Dean’s entire day not getting to see Cas when he got home and vent about the day. Maybe he was getting too reliant on Cas always being there, but they were best friends. Was that a bad thing? 

“I didn’t want to be in the way though.” 

It made Dean frown to think that Cas was uncertain about his place. He knew the other boy didn’t have much in the way of friends or family growing up, but it killed Dean to think that that experience led Cas to feel like he was intruding on someone else’s time if he stuck around. 

“You wouldn’t be in the way. Okay? Besides, Sam loves having you around, especially because you’re the only other mega nerd like him.” 

“He’s your brother though. You should get to have quality time with him.” 

“Cas, you’re a part of my family too. I don’t want you to think you’re ever not welcomed.” 

“I appreciate that. Really. Thank you.” There was something soft in the way Cas looked at him then. Something that made those pesky feelings deep in his chest stir a little but Dean being Dean couldn’t allow those feelings to surface. Instead, he deflected. 

“Is that the only way you’re gonna thank me?” It was just a joke. He even threw in an over the top wink just so Cas wouldn’t think he owed Dean anything for being nice. 

Cas knew but ignored it anyway. “Forgive me. Might I try and thank you properly?” 

Dean just laughed and rolled his eyes before immediately biting his lip when Cas sank down onto his knees and crawled in between Dean’s legs. Dean’s breath hitched when Cas’s fingers slid under the waistband of his pajama bottoms and started tugging. 

“Oh fuck…” 

The blue-eyed boy was laser focused on his task, getting Dean out of his pants and underwear before engulfing Dean’s cock in his mouth. And holy shit it was so good. Always so fucking good. How could it feel so fucking good every single time Cas put his mouth on him? 

Suddenly his mind flooded with Sam’s words. 

_You’re just thinking with your dick. _

_Are you using him? _

_What are you going to do when you lose the only real friend you’ve ever had?_

_Cas deserves better. _

It was like ice water had been tossed over him. 

What the fuck was he doing. 

Should he even be doing this right now? 

Was he using Cas? 

No! Hell no. He’d never do that. But… had they crossed a line? 

Dean knew where this blowjob was leading. He knew it would only be so long before he lost his control and flung Cas onto the couch and sunk into him. 

Before it was… experimenting. Playing around. But now—now that they’d gone the full nine yards it was foreplay and foreplay led to sex. And as much as he wanted to keep having all the sex with Cas he could, he didn’t know if he should. 

The thoughts swirling through his mind made it almost impossible to enjoy the swirling of Cas’s tongue around the head of his dick. 

Apparently, Cas picked up on it. “Oh. You’re... you’re not into this.” A deep flush of embarrassment seemed to overcome his friend and Dean scrambled to reassure him. 

“I want to be. Trust me. I really, really want to be. But... I’m just.... I’m sorry, man.” 

“No. No. I should have asked. I shouldn’t have assumed.” 

Cas honestly looked mortified and Dean felt like an even bigger shithead. He stopped his friend from moving away from him by grabbing him gently by the arm and having him sit next to him on the couch. “Hey, stop, look at me. Ninety-nine percent of the time I’m gonna want it and it’s all I’ve been thinking about but today I just.... Sam and I got in a fight.” 

“Oh? About what?” 

“Nothing you need to worry about. Okay?” 

“I’m going to worry about it though.” 

He didn’t really want to talk about it but he knew if he didn’t give Cas some sort of honest answer his friend was probably going to take the lack of Little Dean being in the game personally. 

“We just disagreed about something and he made me feel like a shitty person about it. And maybe he’s right.… I’m worried he’s right.” 

“You’re not a shitty person. I know that with certainty.” 

That look was back in Cas’s eyes and Dean wanted nothing more than to pull him into a crushing hug and not let him go. “Thanks buddy.”

“Of course.” 

He felt something tight in his chest now that they were just sitting there. He wanted Cas but he just… he felt like he just needed to be closer to him more than have sex with him. 

“Do you… do you wanna just lay down together for a little?” 

Of course Cas look confused and gifted Dean a slight head tilt. “But we didn’t…” 

“Oh, right, duh. Sorry. It was stupid to ask.” Of course Cas didn’t want to cuddle. That wasn’t part of their rules. Sex and orgasms led to cuddling. That’s all. 

“No it wasn’t.” 

“It wasn’t?” 

“I’d like that. To just—to just lay down for a little while.” 

Immediately something unclenched in Dean’s core. “My bed?” 

“It has the superior view to the TV.” Cas agreed. 

“Yours doesn’t even face the TV.” 

“Exactly my point.” 

This wasn’t like any other time and he was suddenly nervous. All those times they’d been basking in euphoric bliss and were too tired to move an inch. It was easy to chalk up falling asleep wrapped up around another to the vigorous sex but now was it acceptable to hold Cas all night? 

Why did Dean want that so badly? 

“How long—how long do you want to rest for?” He asked, fishing for some set of parameters for what would or wouldn’t be allowed. 

Cas seemed just as unsure as Dean was. “Until the end of the movie?” 

“Okay.” Dean agreed easily. 

Cas was asleep before they’d met all the main characters and Dean couldn’t deny the warmth that flooded through him at the sight of his sleeping friend.

* * *

Sun, Nov 26, 2017 7:36

_Dean:_ You’re coming to breakfast with me whether you want to or not. I’ll be at Benny’s in 5. 

Cas was still passed out in Dean’s bed as Dean made his way out the door and to his car. He almost wished he could just stay in bed all day but he knew he had to face his brother. 

He drove the few short minutes to Benny and Ash’s house before driving him and Sam to a nice diner a few miles away. 

They didn’t talk the whole way there nor once they sat down and perused the menu. 

It wasn’t until food was set in front of them that Dean managed to speak. “Sam, look. I don’t want you to think I’m some sort of bad guy okay?” 

“I don’t I just… I really like Cas. He’s a good guy.” 

Dean gave his brother an exasperated huff. “You think I don’t know that? The guy is my best friend Sammy and I don’t say that lightly. He’s family to me.” 

“Then why are you doing this?” 

“He asked me to.” 

“But why did you agree?” Sam had a way of dragging out anything Dean suppressed. The kid didn’t like when Dean kept secrets from him. Even the stuff Dean tried to keep a secret in order to protect his younger brother from memories of alcoholic abusive parents. Sam didn’t let Dean keep things locked away. Hell, none of his family did. But Dean was stubborn as a mule and wanted to ignore what he knew was the truth for longer until he was good and ready. And he just wasn’t good and ready right now. 

“I don’t know…” 

“Dean… You do know. You just don’t want to say it. If he’s your best friend, then why would you do something that you know could ruin your friendship?” 

Dean stared at his pile of pancakes like they’d personally caused all of his problems. It was hard to get the words out and sound confident at the same time. Instead he knew he sounded meek as he tried to explain to the best of his ability why. 

“I didn’t want him to ask someone else. I didn’t… I didn’t want him to get hurt by someone who wouldn’t take care of him the right way or treat him the right way. Or—or just use him… I wanted it to be good for him… special for his first time, you know?” 

He couldn’t make eye contact with his brother yet but he knew from experience the kid was giving him the most pitiful puppy eyes. 

“But what if they didn’t use him? Wouldn’t it have been better if he could have done this with someone who might have wanted a relationship with him?” 

Dean’s heart suddenly thrummed in his chest so hard he thought Sam could hear it across the table. 

He couldn’t say anything. 

“Oh. You want a relationship with him.” 

He didn’t know what to say. He didn’t even think his mouth could form words with the way his heart was suddenly trying to break his ribs but before Sam could say anything more Dean managed to answer with the faintest whisper. 

“…Maybe.” 

He could feel the pounding in his ears as he finally accepted what he’d just said. 

Maybe he did have feelings for Cas. 

Maybe he did, quite a lot. Really real feelings. 

“Does he know that?” Sam asked after giving his brother a moment to stew. “Have you told him?” 

Dean actually scoffed. Who was his brother kidding? Had Dean told Cas? He wasn’t an idiot. He’d barely even accepted it for himself. But telling Cas? That was a recipe for getting Dean’s pathetic little heart to get crushed. 

“Hell no. He just wants to learn how to have sex. He doesn’t feel anything for me in that way and plus—I’m not someone he’d want to date. He should be with someone a lot less closeted than this.” 

He was coming around to it. It’s not that he didn’t know before but he didn’t acknowledge it. How could he, living in South Dakota all his life? It’s not something you went parading around. He knew his family was more liberal than most in their hometown, he’d never once heard anything derogatory towards any type of person, not even muttered behind closed doors at the dinner table. It’s just… he had to get used to letting himself think it all. 

He’d done the whole dating girls thing. He liked it. He’d done the whole sleeping with girls thing. He liked that too. It was enough before but now? Yeah he’d still be up for that stuff if it weren’t for the fact that he had something better already. 

It just sucked knowing he wouldn’t be able to keep what he had forever. 

“Dean, he gave his virginity to you. I think he probably feels something…” 

Yeah Cas probably felt _something._ Dean knew he felt gratitude towards Dean helping him out. Cas felt more confident now that Dean was working with him on asking for what he wanted. His friend felt trust towards him also, how could he not when he was letting Dean know him in a way no one else had. But feelings? Romantic feelings? It was obvious he wasn’t feeling those. 

Fuck. Dean had to be the one to ask him just to cuddle last night and it was clear Cas only agreed because Dean had been down in the dumps earlier. 

The guy never even touched him if it didn’t lead to sex. 

“It’s just sex for him, Sam. That’s all.”

**Notes for the Chapter:**

> Yikes. Was Sam too harsh? I guess I wrote him a little like the teenagers I used to know. When I was that age I might've been a little righteous too and knew "what was best for everybody."
> 
> The next chapter has one of my favorite scenes/conversations I think I've ever written. (Spoiler: It does not include any love confession. I'm sorry).


	11. December 1, 2017

**Notes for the Chapter:**

> Dean talks about his childhood trauma after when he and Cas are in bed, near the end of the chapter if that is something anyone wants to avoid.

Sam had left a few days ago and things had been off and it was starting to make Cas worry that he’d done something wrong. 

Right before Sam had hopped into the car for Dean to take him to the airport, he’d pulled Cas into a farewell hug and whispered in Castiel’s ear to be careful and to make sure he was taking care of his heart. That statement alone had Cas wondering what Sam figured out during his stay but what really threw Cas off was how off Dean had been acting since Sam left. 

It’d only been a few days, really, and not enough time for Castiel to be certain but he felt in his gut something was up with Dean. He’d talk to Cas but wouldn’t say much and his mood wasn’t as light as it had been before Sam arrived. It wasn’t drastic but it made Cas wonder if he’d done something wrong. 

Sex hadn’t come up since Sam left either, which definitely, completely, totally blew. It was mostly Cas’s fault really; he’d been a little too in his head, too scared that Dean wouldn’t want to do anything like the last time he’d tried and he couldn’t bring himself to even ask. 

He’d pretended like it hadn’t bothered him that Dean wasn’t interested that night but he was only human… it was definitely a zap to his confidence. They’d been at it for a while now and it was only logical that Dean was growing bored. It wasn’t like Castiel was as enticing as any of the females his friend had been with in the past. He wasn’t unattractive to most but to Dean he probably was. It wasn’t Dean’s fault he wasn’t attracted to him. It was reasonable that he’d grow bored with being with the same person over and over again if he didn’t find them visually appealing. 

That wasn’t the only change Castiel noticed. There seemed to be a distinct lack of touch between them. It’s not that Castiel was so much a tactile person and needed human touch constantly but he’d gotten used to the amount of times they’d sit pressed up against each other’s sides while watching a movie. And…. 

And the night Sam and Dean had been in an argument and Dean asked to just lie together, Castiel might have hoped that that sort of casual intimacy would become a norm between them. Except it didn’t. Castiel’s beanbag chair was back to knowing the contours of his body too intimately. 

Maybe it was all nothing. Maybe he really was just in his own head as it had only been a few days but self-consciousness was a bitch and made all humans a little nutty at times. He, unfortunately, was no exception. 

Cas figured it was probably time he put on his big boy pants and talked to Dean about what was happening between them, where they stood on their arrangement. He’d understand if their time had come to an end and Dean wanted to go back to being strictly friends sans the benefits—disappointed of course, but he’d understand. 

It made him sad. 

That was plain. Especially the knot in his chest where he knew his heart should be. 

He thinks—he _knows_—somewhere deep down he’d hoped that Dean would… fall for him, perhaps? Or realize that maybe he and Cas had something more than just friendship, that they could give it a try. 

It wasn’t logical, obviously, but it didn’t make him want it any less, and it sure as hell didn’t make it not sting a little that he’d never have it. 

He couldn’t deal with it right now though, he had homework to do and Dean would be home within the hour. They were still on speaking terms, they were still best friends, and that came with the knowledge that Dean could sniff out an upset Castiel from a mile away. It was best to put his focus into something other than his own self-pity. 

He tried his damnedest to focus on the computer screen in front of him but eventually it felt like his eyes were attempting to punch their way out of his skull, a feeling he’d be more than happy to never experience again. He slapped his laptop shut and stretched over to flick the lights off, rubbing at his temples as he sat at his desk. 

Who knows how long he’d been sitting there before the door to their room opened and Dean called out, “Cas?” without receiving a response. “Why’s it so dark in here?” 

All he could do was groan when the lights flipped back on. His head was hurting far more than it had when they’d turned off. Just what he needed. 

“Whoa, what’s going on?” Dean asked with concern in his tone. Cas felt guilty for making his friend worry for him, but damn he didn’t feel good. 

“Head hurts.” He managed to answer. Instantly the lights flipped back off. He heard Dean’s feet pattering around on the floor, the tap running, and the sound of pill bottles being shifted on the shelf. He felt Dean’s hand on his shoulder. 

“Come to the bed.” He said lightly, guiding Cas over to his bed. When Cas was under Dean’s covers a few pain relievers were popped into his hand. “Take these.” Dean said, followed by a command of, “Water” and “Lay down.” 

When Castiel thought Dean’s mother-henning antics were over, his friend gently tapped him on the hip and said, “Scoot.” 

A few moments later Castiel was curled into Dean’s side with his head on his shoulder. 

“When did it start hurting?” 

Castiel sighed into the feeling of Dean holding him, hoping that the sound came off as one of long suffering from his headache at not relief of being so close to the other man again, “An hour or two.” 

“Where does it hurt?” 

“Everywhere.” He groaned. 

“Feeling nauseous?” 

“No.” 

“The painkillers should kick in soon.” 

“Thank you.” 

He felt pleasantly warm at the moment, an obvious contrast from his thoughts from before but still not enough to keep his mind from swirling. How was it in a few hours time he went from fretting over Dean’s lack of touch to reading into the reasons Dean was allowing him the comfort of his arms? Where did they stand? Was this a gesture out of friendship or out of their arrangement? Had Dean, too, noticed that they’d hardly touched one another in the near week that Sam had been gone? That it’d been two since they’d had sex? 

Was it always like this? The feeling of uncertainty with one’s sexual partner? Was there always a level of doubt and confusion between where the two stood? How did normal people circumvent these issues? How did others navigate their way through unclear signs and all the unknown factors of an arrangement? 

Would it lessen if he were to be in a romantic relationship or would the insecurities still lie beneath the surface? 

How did people do this? 

Maybe he knew how. 

If anyone felt even a fraction of what he felt as he was granted the comfort of Dean’s arms around him, then he knew how people could do this. The sound of his heartbeat under Cas’s ear, the feeling of his chest rising and falling against his cheek; the thought that this was a moment just for the two of them, a moment no one could take away because no one else existed—Castiel knew how people could do this. 

If only he had the permanency of a relationship that others were gifted. 

For now this could be enough. It’d have to be. 

His thoughts were starting to grow fuzzy as his eyes started to droop. He almost didn’t notice Dean shaking him. 

“Hey, don’t fall asleep yet. Drink some more water.” 

With a deep yawn, Castiel lifted his head up enough to reach out and comply with Dean’s wishes before he flopped back down to his spot on Dean’s chest, passing out less than five minutes later. 

He woke up in parts, his mind not quite ready to be extracted from his dreams but his limbs feeling the pleasant ache of a nap well received. His sense of smell, pleased that he’d woken up against Dean’s pillow, led to the realization that Dean himself was no longer next to him in bed. He smiled despite himself, knowing that he must’ve been passed out so deeply that Dean had slipped out of bed without disturbing him. Dean did say that he slept like the dead sometimes, especially when he wasn’t feeling great. 

He grunted sleepily as he tried to will his eyes to finally pry themselves open. 

“Feeling better, sleepyhead?” 

He blinked a few times to see Dean standing over him, a slight look of concern crossing his features. Castiel was still too asleep to form words but nodded his affirmation against Dean’s pillow, snuggling just that much further into the warmth of the bed. 

“Here’s more water.” Dean said softly, handing him a glass. Castiel slowly titled the cool liquid into his mouth, not quite trusting his limbs to keep the bottle steady if he moved much faster. After a few steady gulps he pulled the drink from his lips, allowing Dean to grab it and set it on the windowsill. 

“Thank you.” Castiel managed to say after a few throat clearing coughs. 

“How’s your head?” 

“Better.” 

“Good.” 

Castiel was loath to remove himself from the bed but he knew that he couldn’t lay there forever. A quick glance at the clock told him it was already past six thirty at night. If he stayed it bed and tried to sleep again he’d probably be awake by four in the morning the next day, if not earlier and it’d throw his entire day off. 

After a few beats he managed to haul himself up to the side of the bed, with Dean keeping a watchful eye on him as if he might fall off. 

“I think I’ll take a shower.” Castiel asserted, finally pulling himself up to his feet. “Wake myself up again.” 

Dean clapped him on the shoulder as Cas made his way towards their bathroom. “Sounds good.” 

Castiel had never been one of those people (people like Dean) who felt alive and whole and like the world had just sprouted rainbows after taking a shower but he couldn’t deny that the water felt a lot like heaven on his skin at that particular moment. 

He had a smile on his face as he thought about his friend in the other room. How could such a good man exist in his life? There had been no necessity for Dean to be so kind to him like that. A normal friend would be concerned, of course, but to the extent Dean had? To dote on him and hold him as Castiel caught up on his sleep? That had to mean something right? Of course they were friends and Dean was looking out for his wellbeing but… 

Who was he kidding? He knew that was all there was to it. Dean Winchester was a dream friend. One whom anyone would be lucky to have in their lives because he’d go to any lengths to take care of those he cared for. But Castiel couldn’t, though he tried, squash his fantasies’ desires to read the situation as something more. 

His fantasies about the other man were probably what got him into this whole situation to begin with but how could he make them stop? 

He just couldn’t. Plain and simple. 

Even now, when he wasn’t certain what Dean wanted with him anymore, Castiel still couldn’t squash the burning desire in his gut. 

How could two weeks of no sex feel longer than the twenty-one years he’d gone before? Was he pathetic? 

There was a brief moment as Castiel exited the shower that he contemplated putting on pajamas, not wanting to seem like he was suggesting anything to his roommate. But he and Dean had long since forgone bringing a change of clothes with them into their bathroom and instead found no reason not to change in front of one another since they already saw each other naked almost daily. He didn’t see the point of changing it now. 

Plus… maybe if Dean were to see him naked it would spark something in him? 

Castiel felt a little like an idiot as he quickly ran through the pros and cons of just sucking it up and asking Dean if he wanted to have sex. 

He knew he had to broach the subject at some point. Granted he didn’t need to do it naked, but he felt like asking “do you still want to have sex with me” while naked might garner him a response he was more amiable to. Not that he wanted to pressure Dean into doing something he didn’t want to, but…. The alternative was asking Dean, fully clothed, if they should continue their arrangement and facing the possibility of Dean saying no. 

He didn’t know what to do. 

He wanted Dean still. So badly he felt a little like he was going to explode. He wanted to believe that Dean wanted to continue having sex with him too, that maybe Dean just hadn’t thought of it these past couple of days and that it was all a simple misunderstanding. 

Castiel wished Dean would take the lead here, give him even an inkling of a sign to follow but he had a feeling that wouldn’t happen. Somehow he knew it was completely in his hands and he had to be the one to ask, but the fear of rejection was almost too much. It was true that Dean had never rejected him outside of the incident a few days prior and he only turned him down because he was upset about Sam. But now that he wasn’t upset about Sam, what was holding him back? Did he think that Cas didn’t want to sleep with him anymore either? Were they both too timid to broach the subject? 

But why would Dean even be scared? Didn’t he know Cas wanted to sleep with him? 

Maybe it was fact that Castiel needed to have some sort of answer, or maybe it was the fact that he’d not had sex in over two weeks and wasn’t too fond of abstaining from it that had him trifling through a few facts of the matter. 

First, Dean currently seemed to be in a great mood. Secondly, Castiel was horny as hell and it was a reasonable assumption that Dean may be too, which meant they’d both be mutually satisfied if he did go ahead and ask. Thirdly, Castiel was already naked and it would only take getting Dean’s clothes off to get them where he needed them…. 

Should he? 

He stood next to his set of dresser draws, contemplating taking out his pajamas when he heard himself ask, “Dean?” 

“Yeah?” 

He turned to his friend on the couch and tried to fight the flush creeping up his neck as he stammered out, “Can I—do you want to…I don’t know if you want to but I—I was just…” 

He quickly turned away. 

Never mind. He couldn’t do it. Just the thought that maybe Dean had grown bored of him was enough to shut Castiel up immediately. No matter how pent up he felt he didn’t want to have to hear any sort of pitiful rejection from his friend. They were probably just done and that was fine. It was fine. It’d be fine. 

“Cas?” He could see out of his peripheral vision that Dean had gotten up off the couch and was hovering in the middle of their room. He seemed at a loss of whether he should approach Cas or not. It made Cas feel hot with embarrassment. Dean wasn’t an idiot; he had to know what Castiel was asking for. 

“I’m sorry. Never mind. I don’t know what I was saying.” Castiel tried to brush off, looking through his drawer of pajamas with stark intent. 

“You sure?” 

“Yes, of course.” 

“You—you didn’t want to ask me anything?” 

“O-oh, no. It—it’s not a big deal.” 

Was Dean mocking him? Did his friend think it was funny that Castiel was practically failing to utter his request to have sex? 

He couldn’t tell just by the sound of Dean’s voice alone but he also really didn’t want to make eye contact with his friend to find out. 

It was his insecurities coming to play, he knew that, but he couldn’t brush them away as easily as he hoped he could. 

He shivered when suddenly he heard Dean’s voice a few inches from behind him, so close he could feel tendrils of warmth emanating from Dean’s body. 

“Are you sure?” The other man whispered low. 

Castiel felt a hand grip his hip before wrapping around the towel secured low around his waist. A sharp, desperate inhale escaped him. 

“Dean?” 

“Can I?” Dean asked, tugging just gently enough to make sure Castiel understood his intent. 

“Y-yeah.” 

With that he was bare to the cool dorm room air but Dean had him pressed back against his solid form. “How do you want it?” The taller man whispered in his ear. It made Castiel lean back into the touch, heat starting to rapidly pool in his belly. “Cas?”

Different scenarios started flashing through his mind. His bank of Dean-related fantasies were infinite and he had half the mind to ask Dean to pull out his cock here and fuck him against the dresser, but Castiel knew what he’d been wanting for a while now. 

“Can I—can I ride you?” 

“Yeah. Fuck yeah.” Dean pulled away and Castiel followed, obliging when Dean said, “On the bed.” 

Cas clambered onto Dean’s bed and expected his friend to hop on after but instead Dean stood to the side, looking around. “Where’s the lube?” He asked, rifling through a few things on his windowsill and near the bottom of his bed. 

Castiel blushed a little as he partially confessed, “I—I already… in the shower.” Something lustful took over Dean’s eyes making Castiel feel suddenly very pleased with himself. 

The lights were still off in the room except for the bathroom light and the glow of the TV, which Dean turned off as he went in search of the lube anyway, despite Cas’s assurance. When he turned back, the dark, hungry look in his eyes remained but now the yellow glow from down the hallway made shadows cascade over their features as well. 

Dean still made no move to climb onto the bed. Instead he stood next to it as he traced his palms up over Castiel’s calves, moving higher and higher until he was caressing the inside of Cas’s thighs. Cas watched as Dean pulled his hand away and clicked open the bottle of lubricate, pouring some onto his fingers. Castiel knew what Dean wanted then and he pulled his legs open enough for his friend’s fingers to find their mark. 

Castiel couldn’t even put into words how good it felt to have Dean touching him again. He practically melted back into the bed, coming undone just from Dean’s fingers slowly plunging in and out of him. 

It’d been forever. 

He was addicted to this touch, Dean’s touch, and he couldn’t bring himself to care. 

He’d let this man do anything to him if it meant feeling his touch like this. 

And oh how Dean delivered. Castiel couldn’t sense the passing of time even if he wanted to, not with how easily his mind had already turned to mush. Maybe it was mere minutes, perhaps it had been hours, possibly even days before Dean managed to settle on the bed. Cas immediately moved to straddle him, not stopping himself from marveling down at the body beneath him. 

They hadn’t done it this way before and Cas felt his core tremble in anticipation. Oh how he’d imagined it, the way he might straddle Dean on the couch—kissing him for all he’s worth until their clothes came off and he sank down onto Dean’s length. How maybe he’d wake up beside this man after a long night of mind blowing sex only to crave just a little more; how he might shift his leg that was thrown across Dean’s own and kiss all the way up Dean’s torso, waking him up in the process and sealing their lips together; how he’d be so overwhelmed with how much they wanted each other he wouldn’t be able to resist fully waking themselves up in the best way, with Dean’s hands reaching every part of Castiel’s body. 

The things he craved with this man, it was unbelievable. Even when reality wasn’t quite what his fantasies concocted, he still found himself unable to satiate himself. 

It was getting harder and harder to not give into temptations to drag his tongue across every plain of the other man’s body but at least he knew it was acceptable to just touch. He tried to keep it from being too intimate—tried to not linger too much, tried to not be too gentle, tried to not tell Dean how absolutely stunning he thought he was. It was just so hard. 

Tonight was no different. 

He only allowed himself the privilege of trailing his fingers down Dean’s sternum, drawing the palms of his hands over his belly before reaching between his legs to feel his hard cock. It felt like it had been too long for Castiel to want to drag this out, as badly as he wanted a taste of the other man he needed something else more. 

A twin groan left both their lips as Cas raised his hips and lined Dean up with his entrance and sank down slowly. His eyes nearly rolled in the back of his head as he let himself get readjusted to the feeling of Dean being inside of him. It was a few moments later when Dean’s hands moved up Castiel’s thighs to settle on his hips that Cas began testing out a few movements. 

It was new, being in control like this, not having Dean in charge of their pleasure. 

Cas swirled his hips in a circular motion, testing it out and groaning as Dean sank just that much further into him. 

He was unable to speak, hardly able to think as he picked up a rhythm. He must’ve been doing something right if the sounds Dean was making were any signal. His friend’s large hands stayed at his waist, guiding him ever so slightly but neither one of them felt the need to go any faster. 

“Oh, fuck. You look so good.” Dean praised suddenly, making Cas shiver from the words. His eyes fluttered open just enough so see Dean’s eyes tracing all over Cas’s body, seeming to be mostly focused on where the two men were joined. 

“Does it feel good?” Cas asked boldly, too caught up in the moment to feel nervous. 

Castiel’s range of motion wasn’t ideal with him just on his knees but he didn’t want to move. He liked the way it felt with Dean pulling him back down to meet each thrust. He liked the way it felt to let his hands rest of Dean’s chest as he steadily moved his hips up and down. His mind was blissfully empty, only sensation was coursing through him. 

“Amazing.” Dean answered as he shallowly thrust. 

It was so good. Always so good. 

He shuddered a little as Dean’s hands moved to grip his ass, kneading it as Castiel continued to move, only now Dean’s thrusting grew more assertive, quickening their pace. 

Castiel let out a gasp. 

“You like that?” 

“Yes!” 

“Want it faster?” 

“Hng—yes. Oh, fuck, Dean.” 

Castiel raised his hips and held them there, letting Dean fuck into his hole with abandon. His head rolled back and his face tilted to the ceiling as he was overcome with and overwhelming amount of pleasure. He wondered briefly if he could come just like this but knew he’d need just a little bit more to get there. 

Dean must’ve been on his same wavelength. “Touch yourself, come on, you need to come.” 

Immediately Cas did as told, wrapping his hand around his own cock as Dean kept pounding into him. It wasn’t long before he was toppling over the edge and feeling Dean pulling out of him with a primal groan. 

Cas wanted to just collapse on Dean’s chest but had enough wits about him to roll to the side, still partly atop of his friend but too boneless to care. 

He laid there for a moment, trying to catch his breath before turning in towards his friend. As he moved to snuggle into Dean’s side his arm moved through a glob of come on Dean’s abdomen and he pulled back quickly. “Oh, I’m so sorry! I didn’t even—I really didn’t mean to. I’ll clean this up, hold on.” 

Dean chuckled, “Cas, dude it’s fine. It happens. Can’t really help gravity.” 

“It’s still gross….” 

Dean scoffed at Cas’s words and gave him an exasperated look. “No more gross than me coming on you.” 

“But that’s—I’ll clean you up.” Cas had wanted to say that it was different. He’d wanted to say that he thought it was the sexiest thing ever to have Dean’s come on him but he didn’t know if he should. Was it weird to like that? Was it weirder that he wanted to know what it felt like to have Dean come in him? He didn’t know if he’d ever be brave enough to ask. 

It was only a matter of minutes before Castiel had them cleaned up and he was able to crawl back into bed into Dean’s waiting arms. 

“How’s your head?” Dean asked gently, carding his fingers through Cas’s hair with the question. 

“Doesn’t hurt at all now.” 

“Orgasms cure all ailments.” He teased, eliciting an eye roll from Cas. 

“I’m sure it wasn’t the amount of water you made me drink or the nap. Just the orgasms.” 

“Damn right. My dick is magical.” 

“Can it make you less of an ass?” 

“Shut up.” 

Cas settled easily against Dean, but with his two-hour nap from early still so fresh he didn’t feel quite as tired as he usually would post orgasm. He was content here though, content to just breath in sync with his friend, trailing his fingers across Dean’s sternum in random patterns. 

It still baffled him how easy it felt lying with Dean like this. 

As gentle and caring as Dean was with Cas and his brother on the regular, Dean wasn’t generally so casual with his touches with others. It was almost unheard of to see Dean hugging someone outside of his closest friends or family. And Castiel’s friend could maneuver his way out of large crowds so quickly it was almost like he could teleport. 

He knew how lucky he was to be able to have this right now. And whether they decided to end their arrangement in a few days or even a few months from now, he wasn’t going to take a moment of it for granted. Having Dean’s trust like this made Castiel fall even deeper each and every time. 

Dean was a marvelous person. He’d never get over that. 

“I don’t mean this in a negative way at all….” Castiel found himself speaking, knowing Dean wouldn’t mind his stream of consciousness. 

“Mean what?” 

“I—I’m surprised with how comfortable you seem, sharing a bed with someone. It’s just, you always talk about personal space and you never seem to enjoy when people touch you unexpectedly, even just a hug, and I completely understand why—it just made me assume you wouldn’t care to be close with someone in a ‘cuddling’ sense.” 

There was a moment of silence between them before Dean contemplatively said, “Huh.”

“It was just a random thought...” 

“I don’t mind.” Dean replied softly, letting Castiel know his thoughts weren’t unwelcomed. “I think you’re right too. I don’t like being close to people. Sometimes even people that I know really well if they come too close to me I just get, overwhelmed you know?” 

“I do.” 

Dean then turned to lie on his side, facing Cas. The small dorm-sized bed meant their naked bodies were still pressed up against one another but there was nothing overtly sexual about it. 

“Can I tell you something?” 

“Of course.” Castiel responded, scooting just a fraction closer when Dean’s arm draped over his waist and the man’s hand settled on his back. 

“You—you know about my real dad, what he did to me when I was younger…” 

“I do.” 

Castiel’s heart ached for his friend at the life the young man had lived growing up. He’d never wish what Dean had gone through with his father on anyone, and Castiel knew he’d give anything to not have let it happen at all. He’s spent a long of time wishing he could rewrite history and save Dean from such a sad early childhood. 

No one deserved that sort of pain, especially not Dean. 

“It—it took me a long time to let anyone touch me.” Dean confessed sadly. “Even just holding my hand to cross the street. I’d… I’d see someone’s hand reach out to me, even Jody’s or Bobby’s and I couldn’t help but flinch.” 

“I’m so sorry you went through that.” 

“It wasn’t all bad you know?” He asked with a shrug. “Like, I remember happy days with him where he’d lift me over his head and throw me in the air until I was laughing so hard I’d almost pee myself. And I remember him going over parts of his truck, teaching me things, and letting me pretend to drive. And even before he died we had a few good conversations in the rare times I’d see him…. But it never really erases the bad.”

“And that’s fair. What he did… no child should live through that.” 

They both frowned at each other, knowing how true Castiel’s words were. 

“I don’t really remember much. Not anymore.” Dean said, a fraction of relief at his words settled something in Cas. “When I was little though I would have so many nightmares. Almost every night. I’d wake up and always run to find Sam and crawl into bed with him just to feel safe again.

“My mom says she didn’t know what to do for a while. How could she though? What do you do with a kid who was beaten by his only parent, who barely talked to anyone that wasn’t his younger brother, and flinched when anyone even tried to touch him?”

Castiel couldn’t help but pull Dean closer to him, willing his friend to let him share the burden. The soothing touch to his back let Cas know it was appreciated as Dean continued speaking. 

“She’d sit next to my bed, though, every night in a really uncomfortable chair and tell me that no one would ever hurt me again. Sometimes she’d run her fingers through my hair when I’d let her. But she was always there when I woke up, hunched over in that chair, just because I’d always ask her to stay.” 

Tears pooled up in Cas’s eyes but he refused to let them fall. He smiled a watery smile at his friend’s recount of his mother’s comfort. “Sounds like her. You have a wonderful mother.”

“I really do. I’m glad she got stuck with me.” 

“She’s very fortunate to have a son like you. What you had to go through… it—it’s so unfair. Parents are supposed to be the people who love and care for you, not the people who cause you so much pain. I wish you never had to go through that. I wish your father could have been a better man.” 

“It got me Jody and Bobby though.” 

“It did. It still doesn’t erase the pain you went through.” 

“No. I don’t think anything fully will. But I’ve moved passed it. The nightmares still happen sometimes but not like they used to. Just when things get really stressful or something.” 

This was something Dean didn’t often talk about. In all their friendship Castiel thinks he’d mentioned it a handful of times, not liking to confess to the fact that he still had bad dreams. 

“Even now?” He asked cautiously, not wanting to upset his friend.

“Yeah, but rarely. It’s not so bad when someone’s close. I can fall asleep again pretty quickly.”

Cas nodded his understanding but didn’t know what to say but Dean continued to talk. “I used to share a room with Sammy. After my mom realized I’d just crawl into his bed on most nights she just stuck us in the same room together. So I grew up always having someone there if I ever woke up scared. 

“Honestly, I was so fucking nervous about getting a random roommate freshman year. I didn’t know what to expect. I’d always been with Sam, my mom, or Bobby and I didn’t want some random person seeing me having a nightmare and think I was… broken or something.” 

“I’d never think that of you.” 

His words brought a bright smile to Dean’s face. “I know you wouldn’t but I didn’t know that then.” He waited a beat before lowering his voice to admit, “I still get them sometimes but when I do, it’s not so bad with you here. Or across the room, I mean.” 

Something fluttered in his chest hearing that Dean found comfort in Cas’s presence. Knowing he could give that to Dean in any shape and form elated him. 

“Good, I’m glad it helps.” 

“I think being close helps too.” Dean said so lowly Cas almost couldn’t hear him. “I never really stayed over with anyone else before but maybe I would have noticed it then too. I haven’t had one in a long time. Especially not since… all this.” 

Cas would have given anything to be allowed to press his mouth to Dean’s at that moment and let his friend know that he’d always, always be there for Dean—in any capacity the man would have him. He’d spend all of forever like this with Dean fighting any monsters and demons from his friend’s mind, without hesitation. 

But he couldn’t say that. Maybe in another life. For now he could settle with, “Let’s keep it that way then.” 

The look of gratefulness on Dean’s face was enough for Cas. 

At least, in that moment it was.

**Notes for the Chapter:**

> When I first started writing this I wrote Dean a lot more confident/cocky at the start. I had him really eager to hook up all the time, and kind of bossy in the bedroom but I never LOVED that version of him. Cas had started to fall pretty hard but Dean was just so 'meh' to me that it made me not want to keep writing his POV. But then this chapter happened and Dean came out and said all of this and it was like I finally found the Dean I needed to write and I felt like I knew where I wanted the rest of this story to go. I just really loved the ending of this chapter and I really love Jody in this work too. You guys haven't met her yet, but even from this chapter alone I think it's clear she was the mama bear Dean and Sam needed.


	12. December 2, 2017

“You’re done being a hermit this weekend. You’re coming out with us.” 

Dean groaned into the beer bottle he had just brought to his lips. He knew Benny had timed that perfectly for Dean to be unable to respond but he swallowed his drink quickly and scowled at his friend. 

“Dude, I don’t want to go out. Me and Cas were going to watch Star Wars before Last Jedi comes out.” 

“You have more than a week to do that! Bring Cas out with us, but so help me you’re getting out of your shoebox. Come on dude, we never see you out anymore.” 

“Maybe because that shit sucks.” The thought of going out and enduring the Vegas nightlife had Dean already feeling overwhelmed. What once had seemed awesome as a young freshman had quickly lost its appeal. Vegas didn’t do anything small and neither did his friends when they had the itch to go clubbing, which meant he’d be in for a long ass night. 

“Oh, so sitting at home with Cas watching Desperate Housewives is better?” 

“We prefer Gilmore Girls, thank you very much.” 

Benny wasn’t deterred from his pestering. He had a mission to get Dean out on the town and Dean knew there was no sense in putting up a fight. Especially when Benny seemed to be getting everyone in on the event. 

“Hannah is already telling Cas he’s going out, so you better get your shit together too. This Friday…. we’ll go to Coyote Ugly just for you.” 

“Fine! But only for a few drinks. I’m not getting wasted.” 

“A few drinks will still get you lucky, with a face like that.” 

“Nu uh. No hook ups either. I’m done with that.” 

Dean had mentioned the ‘no hook up’ thing a while ago to his friend but apparently Benny hadn’t taken him seriously. Or maybe he did since he suddenly stopped trying to tease Dean and looked at him with a curious stare. 

“For real?” 

“Yeah? Have been for a while.” 

“What’s changed?” 

“Nothing’s changed.” He shrugged, hoping Benny would pick up on his lack of desire to talk. 

“The Dean I know loves sex. Now he’s done with it?” 

He tried to laugh in agreement but knew it wasn’t reaching his eyes. It sucked knowing that most of the people around him assumed that he was some sort of sex-addicted man-whore. But there wasn’t much he could do to change their minds not when changing their minds meant confessing to a pretty steady rela—_arrangement_ with him and Cas. 

He tried brushing it all off with a joke. “Maybe I’m saving myself for my soul mate, ever think of that? That I wanna be pure and revirginized for them?” 

“Or you just struck out one too many times and knew to throw in the towel.” 

“Fuck off.” 

Something in the way he said that must’ve clued Benny into not pressing the matter further. Instead he clapped Dean on the shoulder as he went to grab another drink. 

“Seriously, go out with us. It’ll be fun.” 

Dean still didn’t want to go out but knew from Cas’s text that read: _Hannah said we have to go out with everyone this weekend,_ that there really wasn’t a choice. 

“Fine.” 

He couldn’t remember the last time he’d even gone out to a club. He liked to hit up bars every so often but bars were way different. The thumping music, the hoards of people, the lack of any personal space—it wasn’t his scene. He didn’t particularly like being dry humped by a slew of strangers no matter how much people probably assumed he did.

It was a comfort knowing that Cas would be dragged into the mess too. Especially after their talk a few days ago, it was nice knowing that Cas wouldn’t leave him surrounded by strangers for any reason—not that Cas ever had before but now it seemed guaranteed that his friend would look out for him. 

He wagered that Cas was about as stoked to go as Dean was. It was their first time in what seemed like months that they’d even gone out apart from grabbing some food with Hannah a couple times. 

Maybe it did make them hermits to enjoy sitting in most days but unbeknownst to their friends they weren’t exactly just bumming it on the couch. And now especially, when it felt like they had just gotten back on the same page and were finally having sex again—Dean was not keen to have anything come in the way of him… well, coming. 

It was just one night though. He could handle it.

* * *

Unavoidably, the weekend rolled around and they found themselves pre-gaming at Benny and Ash’s with a whole slew of people Dean didn’t know most of. Friends of friends who were invited with a promise of drunken shenanigans, people Dean wagered they wouldn’t see neither hide nor hair after mooching off the free booze at the house. 

And free booze there was. With the amount of alcohol the boys had available, it was a wonder they hadn’t started up their own bar already. Ash, despite his generally questionable taste in foods, was quite the bartender for the group, dishing out drinks that could rival even some of the clubs. It was no wonder that after a few cocktails that Dean was already feeling a bit loosened. 

Eventually—after everyone was bordering a little too tipsy—they all piled into large shuttles, stacked on top each other to keep from spending an arm and a leg going out on a weekend. Dean somehow managed to be stuck with a lapful of some girl who he’d never met—Kate or something like that—who was way too drunk and handsy for his liking. Cas wasn’t fairing much better with Kate’s equally drunken friend who Dean affectionately named Kate-two attempting to whisper something in his friend’s ear. 

He felt a little bad for the girl, trying so hard to woo Cas. He didn’t blame her in the slightest, he knew what those blue eyes could do to a person but the poor girl had no clue just how uninterested Cas was in what she was offering. He preened a little on the inside realizing that even though he might not be Cas’s preferred male to be hooking up with, at least he was doing a damn good job in keeping his friend satisfied for the time being. Kate-two just didn’t have what Dean had to offer. And she was a chick… but that was beside the point. 

“What are you smiling about?” Cas asked, just now noticing Dean looking at him. 

“You and your new friend seem to be getting along.” 

Dean eyed Kate-two who was giggling with Kate-one about something. Both girls turned to look at Cas and Dean at the same time and giggled again. Dean knew they were too drunk to contain their enthusiasm but it still amused him to no end how unlucky these girls had gotten sitting with the two men in that particular vehicle that they weren’t able to strike lucky with. 

They pulled up to the first club with a jerk and practically fell out of the car. The line inside the casino was ridiculous but most of their party seemed set on sticking it out even though the cover fee was just as obnoxious as the line. Dean opted to pay for Cas’s (it was quicker than each paying separately, obviously) and then they were in. 

The club was dark and the bodies were plenty and Ash had somehow procured three shots for everyone in what seemed like record time. 

He sent a prayer to whatever deity he could think of that would get him through the following morning unscathed and sank each shot quickly—definitely feeling the effects of all the alcohol in his system already. 

Kate-one and Kate-two had long since disappeared and the rest of their group had seemed to clump together in odd cliques, leaving Dean to stick by Cas’s side as he preferred anyway. 

Inch by inch they all seemed to be moved from the outskirts of the room and coerced closer to the center of the dance floor into the hoard of gyrating bodies already packed in like sardines. 

He was already too drunk to feel like crawling out of his skin by the vastness of the crowd, almost numb to it. It helped to have Cas’s steady presence at his side as shadowed faces and foreign bodies pressed against him in passing but his mind wasn’t focused on the others. 

He could smell Cas’s cologne still, even against the swarm of others around him. It didn’t take him long to realize that it wasn’t due to his uncanny ability to pick Cas out in a crowd but the fact that he’d somehow managed to press up against his friend’s back, moving in time to the music. He didn’t know how he’d gotten there but allowed it to happen anyway. With the lights in the club no one could even tell that he’d moved his hands to his friend’s hips. No one could tell that he’d pulled Cas back against him. No one could tell that he had no intention to leave an inch of space between them for as long as he could manage. 

He knew Cas could feel the press of Dean’s dick against his backside, what with the way his ass eagerly pressed back—shifting side to side in time with the music. It was hard to restrain himself from giving in to exactly what he wanted but he resisted, knowing their friends were too close for him to get away with everything. His mind was going crazy though. He wanted more than anything to wrap his arms fully around Cas’s torso—to nip at the crease of his neck and see how he’d respond. 

Inebriation supplied him with a slew of fantasies of what the two of them could get up to if their friends weren’t there. What if he brought Cas out just the two of them, what kind of shit could they get up to? With this many bodies—with the lights so dim, it wasn’t exactly a secret the people got up to less than chaste acts of conduct on a dance floor. Dean saw the appeal. 

How badly he wanted to just slide his hands up under Cas’s shirt or under the waistband of those tight pants—test the limits on what they could get away with in the dim club lighting. Could Dean get his hands around Cas’s dick without anyone noticing? Would Cas even like that? Would he be into fucking in public? 

But mostly would Cas be into Dean touching his dick? 

He’d been thinking about it more—a hell of a lot more. He wasn’t scared of touching it or anything—a dick was a dick. Even if he hadn’t touched one before he still knew how one worked but it being _Cas’s_ dick made it different. That made it important. And really fucking hot. And Dean really wanted to know what it felt like. What it tasted like. But was he even allowed to touch him like that? Cas never asked. 

That was one of the biggest struggles Dean had with their arrangement. Why did Cas never ever ask for the things Dean wanted? 

Why didn’t he ask for kisses? Why didn’t he ask to have Dean touch his cock or suck him off? And fuck! Why didn’t he want to touch Dean’s ass? 

But mostly… Why was he so fucking sexy dancing like this? Was it his goal to get Dean hard? Because dude… 

Mission fucking accomplished. 

Dean knew he was well past wasted—definitely approaching sloppy drunk. He had no clue how long they were even on the dance floor. It could have been minutes it could have been hours but Dean was too fucking gone to pay attention to anything other than Cas against him. 

He wanted to fuck so badly. He could feel it burning deep in his gut and was honestly weighing the pros and cons of dragging Cas off to the nearest restroom and having his way with him. He only barely managed to resist it when Hannah’s voice came screaming in his ear, making his eardrum ring uncomfortably. 

“We’re gonna go! This place is too much!” 

“What?” He yelled back, tugging Cas’s attention to their friend. 

“We’re leaving! Let’s go!” 

His mind was swimming as they made their way out of the crowd. The world didn’t feel real to Dean as they moved past each stranger and through the flashing lights. He stumbled over his feet with nearly each step and didn’t realize until they were outside that Cas’s had all but held his weight through the hallways of the casino. 

A gust of wind hit them as they walked out the front doors, the cool air doing a lot for Dean’s mental clarity but his downstairs friend was still trying to make an appearance. He huffed a few breaths before moving a little ways away from the group to lean against the outside wall and catch his breath. He was thankful that Cas decided to come with him. 

“You doing okay?” 

Dean grunted in a non-answer. 

“A little too much excitement in there?” 

He looked up from his shoes to glare at his friend but the glint in Cas’s eye told Dean the fucker knew exactly what he was doing on that fucking dance floor and had no regrets. It’d be hot as fuck if Dean didn’t feel like he was a few moments away from puking. 

What the fuck had he been drinking?

The remaining members of their group spent a few minutes arguing over where to go next, with Benny and Ash hankering for another club but the majority of them needing something a little more low-key than what they’d just endured, something with greasy food and less sugar-rich drinks. They settled on shuttling over to a pub near the school, far more in their comfort zone with an honest to goodness late night bar menu to boot. 

Despite Dean hating clubs, he already missed being able to pull Cas against him without anyone asking questions. And from the way Cas kept stealing glances and looking in the general area of Dean’s dick… he was pretty confident Cas was missing that dance floor too. Neither of them complained as they entered the bar and found their way to a high top but their stolen glances were enough for both of them to know what the other had in mind. 

Dean couldn’t wait to sneak out the minute their friends wouldn’t find it quite so suspicious. 

They were down about eight people now—having lost them at the club and the remaining of them were drunk to the point that no one seemed to question why Dean kept invading Cas’s space… or why Benny and Hannah were actually making friendly jabs at one another. It suited him just fine. And if anyone asked—Dean was just tired and Cas was nice to lean against. That’s all. 

No one cared though. All too caught up in ordering their next round of drinks and ordering a truck load of chicken wings and curly fries—which to be fair were probably the only two editable things at the place. 

Dean had spent a good amount of time at this particular joint over the years. He liked coming here with his friends to watch a few games or just chill with some beers but on some other occasions he’d found himself here with the intent of something less wholesome. Here, girls were less likely to show up with their cliques of over-excitable friends who giggled every time a dude even looked their way. The girls here seemed more laid back, would come to hang out with their friends and sneak away to talk to a guy they were interested in. They seemed to know what they wanted and were more direct with those wants. 

It wasn’t too frequent that he came here to search for a hookup but the nights he did there were generally the same girls lingering around that seemed to regular the place for reasons of their own. It’s why he wasn’t exactly shocked to see Lisa Braden hanging around the bar scouring out her next flavor of the night. She was one of the girls Dean had a few hookups with about a year or so ago. They’d shared one freakishly bendy night together which was just enough to satisfy Dean’s needs at that moment but she’d still been around the bar a few times that he’d come back. 

It was obvious that she was more interested in what he had to offer than he was in return and he knew better than to make sex with her a frequent thing—his gut telling him she’d want a relationship out of him—but he wasn’t a saint either. He might have offered to assist her a few times but never did go all the way with her again apart from that first time. 

And as fun as she was she just didn’t really do it for him, he learned that after a few too many back seat hookups. So, he’d gone and been a complete ass, going AWOL eventually. 

Actually looking back—she was the last girl he’d been with before things kicked up with Cas. 

The thought kind of shocked him sober as he realized that Lisa was suddenly making eye contact with him from across the bar. He cringed inwardly as she scooted off her barstool. 

She wasn’t exactly the kind of girl who was good at being told no. Since he and Cas had started their arrangement, Dean had gotten a handful of ‘booty texts’ from Lisa. Even with him ignoring every one, she was persistent. They were mostly just ‘are you up’ or ‘want to come over’ texts paired with more than a few pictures that Dean didn’t bother looking at. He’d taken to deleting the messages before ever opening them but knew it was high time he just blocked her—feign getting a new number if she ever called him out on it. 

Sauntering up to him smelling thickly of her signature perfume, Dean knew he couldn’t get out of at least talking to her. With Cas right next to him though, Dean wanted to just pretend she didn’t exist. He didn’t picture this moment going well. 

“Dean! I feel like I haven’t seen you in months!” He didn’t know if it was just the amount of time he hadn’t seen her or if she’d always been such a clingy person but with her hands now roaming his chest it made Dean flinch back. She seemed much drunker than he’d seen her before. 

“Yeah I’ve been staying in a lot lately.” He responded, taking her hands away from his body. She frowned at him dramatically. 

“Boo. I’ve been missing you.” 

He turned towards the tabled and grabbed a water to offer her. By the smell of her breath alone he could tell she was pretty wasted and it didn’t take a genius to realize she’d probably had a rough day. She wasn’t quite so excitable most days. 

She took a few gulps of the water before going back to whining, “You never text me back anymore.” 

“Like I said. I’ve been busy.” 

“Too busy for me?” 

“Lisa.” He couldn’t deny that he was worried for her. He knew in no way he could be described as sober but being as large as he was it was unlikely he’d be in any danger if he were this drunk and alone. He didn’t like the fact that she was out at this hour and without anyone to ensure her safety. 

He was nearly too focused on trying to get his phone out of his pocket to really hear what she was saying to him. 

“Come on! I miss you. I know you miss me too. Have you been getting my pictures?” 

By the time his phone was in his hand and one of the ride service apps was up, Lisa was back to slithering her hands up his chest and Cas was speaking in his other ear. 

“Dean, I’m going to go back home.” 

“What? Cas, why?” 

“I’d just rather be at home.” 

“I’ll come with you. Just give me a minute.” 

“No! Really, stay out. Like you’ve said you’ve been home a lot lately.” 

Lisa was clearly listening in on their conversation as she decided to add her own commentary just then, leaning over Dean to speak to Cas. “Hasn’t he? Tell Dean he should come home with me. I bet he’ll listen to you.” 

Cas seemed to be eyeing Dean’s phone as he spoke, “You should go home with her. You two have fun, okay? Bye… Lisa.” 

Before Dean could even protest, Cas was walking out of the bar. And as much as he wanted to chase after his friend he knew Cas was competent enough to get himself home safely. He also knew he couldn’t just let Lisa fend for herself. 

He looked across the table to see which of his friends were sober enough to help him when he saw Hannah giving him a look of disapproval, probably assuming he was about to go hook up with Lisa. 

Despite her obvious disappointment in him he knew she was probably the most responsible out of all of his friends and couldn’t help but ask, “Can you help me Han? I need to order her a ride home. Can you get her to drink some more water?” 

She nodded silently before seeking out an unused water cup from their table and coming over to Lisa. “Hey? What’s your name?” 

“Lisa—you Dean’s girlfriend?” 

“What? No we’re just friends. I don’t think I’m Dean’s type.” Apparently that was enough to get Lisa to drink the water. He let her take a few more gulps before he decided it was high time he actually ordered her car. 

“Lis, can you give me your address?” 

“Mmm, you coming home with me?” She asked as sultrily as she could but the way her eyes seemed too heavy to stay open, it came off more like she was sleep talking. 

It was then that Hannah seemed to lose her look of concern and seemed to understand that Dean really did just want to get Lisa home and had no intent on going to said home with her. 

“Do you live around here? Does your license have your address? We can look at that if you can’t remember.” 

“I know where I live.” Lisa slurred. 

“Can I please have your address, Lis?” Dean tried again, this time somehow managing to get it out of her and typing it in quickly. It was a relief to see that on such a busy night he only had to wait a few minutes to get her tucked into the car. He let Hannah go back to hanging out with their friends as he walked Lisa out to the front parking lot to wait. 

When the car got there, the woman driving immediately looked apprehensive at him as he lowered Lisa into the back seat. He didn’t blame her though as Lisa was practically asleep by that point. What the driver must’ve been imagining he didn’t want to know and he definitely didn’t want to make her more uncomfortable by getting into the car either. 

“Hey, I’m just a friend of hers. Are you good to get her home or do you want me to come with?” 

She looked into the back seat and assessed the situation before giving a kind nod Dean’s way, “I’ll be good to take her. Have a nice night.” 

He nodded at the driver before pulling his head out of the doorframe. “Take care Lisa,” he said gently before he shut the door. 

It was a relief to know she was safe, which meant that Dean was now free to go home. He contemplated getting another ride home but felt like walking would probably burn off the alcohol that was still coursing through his veins. It also gave him a little time to think about the knot that had formed in his gut when Cas announced he was leaving the bar. 

He knew his friend well enough to know the look in his eyes meant he was hurt and had been thinking the worst. Dean wasn’t sure if it hurt more to know he’d hurt Cas or the fact that Cas thought so poorly of him. Did Cas really think Dean could just go home with a random chick just because she said hi to him? He wished Cas would have stuck around a few more minutes to see what Dean was trying to do—to realize that Cas never had to worry that Dean would go home with someone else. 

By the time he’d made it home the driver from the ride had called to confirm Lisa making it back into her house and Dean could relax knowing she was okay. It dawned on him as he pulled out his room keys, that he probably should have stuck around to make sure Hannah got home safely but Benny and Ash were still at the bar and they knew better than to leave her alone. 

He paused to text her anyway, asking her to tell him when she got home. 

Immediately after unlocking the door he kicked off his shoes and shrugged off his coat, ready to be in comfortable clothes again. As he walked down their short hallway he started tugging at the rest of his clothes, assuming that Cas was probably already passed out. 

It wasn’t until he had his shirt up and over his head that he realized a desk lamp was still on in the room and Cas was laying on his bed facing the wall. He appeared to just be surfing through Facebook and didn’t even bother to look at Dean. 

Guilt was still swirling in his gut and Dean knew he needed to set the record straight. He wasn’t inebriated enough anymore to word vomit all his thoughts and feelings but he was able to get the words he needed Cas to hear out of his mouth. 

“I wasn’t gonna go home with her,” he explained point blank. 

“That’s not why I went home.” Cas replied but the slump of his shoulders said otherwise. 

“I didn’t even want to go home with her,” Dean admitted. He felt vulnerable standing in the middle of the room with Cas still not giving him his attention. “I just needed to make sure she got home safe.” 

He heard his friend sigh, “Dean, you don’t have to explain yourself. 

He took a moment to debate what to do. He didn’t know exactly what was happening between them at the moment. Were they fighting? Were they okay? Clearly Cas was upset that Dean had been talking to Lisa but Dean just didn’t understand _why._ Unless he thought Dean was really terrible enough to go home with a girl who was practically unconscious? Or that Dean wanted to break this promise and sleep with other people?

Surely Cas didn’t think those things? And he had to know that Dean didn’t want to sleep with anyone else, right? 

Dean contemplated not saying anything and just going to his own bed but that thought left him feeling even more unsettled. He needed Cas to know that he wasn’t a complete douchebag, even if it seemed like he was. He wanted to believe that Cas didn’t think of him as a complete scumbag but it would just be par for the course these days. 

“Did you think I wanted to go home with her?” Dean asked, knowing he sounded a little desperate. 

“Maybe,” Cas said with a shrug, like it wasn’t a big deal that he assumed Dean wanted to cheat on him. Well not _cheated_ but… to Dean it kind of felt that way. 

“I made a promise to you that I wouldn’t sleep with anyone else, Cas, and I’m not gonna just break that promise without talking to you.” 

He didn’t even realize until that moment how true the statement really was. It wasn’t just a promise that he felt obligated to keep, Dean didn’t _want_ to sleep with anyone else. Not now, not ever. What Castiel did to him, it was everything Dean didn’t know he needed before. Just looking at the man, even now curled up on the bed… Dean was a goner. He wanted Cas in every way he could have him. 

He wanted to be allowed to hold him every night as they fell asleep. He wanted to be able to go to clubs with him and show off the fact that Cas was his. He wanted Cas to never doubt that Dean wanted him. 

But how was he supposed to say that? He couldn’t, not when Cas wasn’t interested in him that way? How could Cas be anyway? He didn’t even have enough faith that Dean wouldn’t break their promises to one another. 

Cas peered over his shoulder, his features more relaxed after hearing Dean’s words. “Okay.”

“Are we—are we okay?” He was still standing in the middle of the room, uncertain what to do with himself. His shoulders sagged in relief when Cas nodded to him. 

“We’re okay.” 

“I’m sorry.” 

“Dean, no. You did nothing wrong.” 

“I still feel bad.” 

“You shouldn’t,” Cas insisted, before unexpectedly saying, “You’re shirtless.” 

Dean laughed at the abrupt change of subject but sucked in a breath when he noticed how Cas’s eyes fell on his bare torso. The look his friend gave was just like the one outside the club and all the want that had filled Dean as he danced against Cas’s body came rushing back. 

His lips morphed into a smirk. “Can I tell you something?”

“Yes?” Cas’s eyes were still on his body and Dean couldn’t resist not giving in to what he’d wanted to do all night. With three bounds across the room, he clambered onto the bed and slid up behind Cas—effectively spooning him for all intents and purposes. 

Bringing his lips to the shell of Cas’s ear he whispered, “I thought I was going to lose my mind I didn’t sneak off with you like I wanted… to show you exactly what you were doing to me on that dance floor.” In a parody of their movements from the club Dean pressed up groin into Cas’s ass, moving in sync to the beat of silent music. “All night I couldn’t wait until we were back home. Just like this.” 

He reveled in the way Cas breathed sharply from his words. It was even better when he moaned out Dean’s name in response, just like now. 

“It feels so good. Can’t help but crave it,” Dean kept whispering not allowing the movement of his hips to stop either. 

“You—you crave it?” 

“All the time.” Not knowing where Cas stood on hickeys, Dean just let himself trail the edge of his jaw along the ridge of Cas’s neck. He smiled to himself when Cas started shifting more eagerly against him and Dean’s need for him grow tenfold. “We haven’t tried it like this have we?” 

“N-no.” 

Like he’d been craving in the club, Dean wrapped his arm around Cas’s torso pulling him more solidly against his chest. He picked up the speed of his hips. “Do you wanna?”

Cas seemed almost satisfied with this grinding they were doing but his need for more must have won out. “Oh—yeah.” 

He’d obviously changed coming back from the bar because where there had been dark skinny jeans hours before were now sweat pants that Dean had to push off along with Cas’s briefs to get him naked. It was a little more complicated getting his own jeans off, what with Cas’s unrelenting grinding back against him yet somehow, one handed he managed to shove them off enough to kick them away. He didn’t care that his socks stayed on. 

He didn’t care about anything other than the fact that he had Cas, here, in his arms and arching into his touch like he wanted Dean as badly as Dean needed him. 

It always felt so good to be touching him. Always tingled down to his toes the moment his skin felt Cas’s body heat against his. Not even with the hottest chicks that he’d fooled around with did he get this burning feeling of need deep down inside of him. He let himself rock between Cas’s cheeks, just to feel the touch of Cas’s body against his and to sort out the haze of _mine, mine mine_ that went racing through his mind.

Now that they were alone he didn’t have to hold back like he did in the club. Now he got to run his hand up over Cas’s thighs and over his hip. He was allowed to pressed the palm of his hand against Cas’s belly and feel his way up to his chest. He even got to run his hand back down, dusting ever so slightly over the thatch of hair under his navel before snaked his hand between their bodies to touch Cas’s hole. He lightly rubbed his middle finger over it, loving the way his friend shivered against him. 

“Where’s the lube?” 

“Mmm... couch.” Cas moaned in answer. 

“Too far.” He concluded, unable to fathom pulling himself away. He decided spit would have to do. With that thought he pulled his hand away and spit enough to coat his fingers before bringing them back to their destination. He didn’t hesitate to start with pressing one in right away and Cas was all too eager to accept it. 

Dean wasn’t lying when he said he was always craving it. But not just craving sex. No. He was always craving it with Cas. It was the best sex he’d ever had. It wasn’t just sex though. It was more than Dean could comprehend. Cas made him feel better than anything else in the world. Nothing could feel better than being with him, Dean was certain. 

“Are you ready?” Dean asked sooner than he usually did but he felt like he was about to explode if he didn’t get in Cas right then. 

“Yes, yes. I’m ready.” 

That was all Dean needed. 

He grabbed behind Cas’s knee to pull his top leg into the air before lining up and pushing in. He did his best not to rush but it took all of his willpower not to shove forward like he wanted to. It was this moment that was always the hardest, where Dean had to fight the urge to kiss Cas senseless, not only to distract him from the feeling of Dean entering him but to show Cas how fucking much it meant to him to be able to have this with him. 

He gave Cas a few moments to adjust before he experimented with his thrusts. 

“Oh—Dean!” 

Hearing his name fall from those lips always woke something primal in him. The way Cas wasn’t scared to say it, acknowledging the fact that it was Dean making him feel this way… he wanted nothing more than to be the only name Cas ever said from pleasure. He wanted every whine, every moan, every shaky breath—all of it. 

“Touch yourself. Wanna watch you touch yourself.” 

Cas didn’t hesitate to fulfill his request. “Mmm.” 

“That’s it. Just like that. Tell me how it feels.” 

“So good. So good.”

“That’s right. I’m gonna make you feel so good, baby.” 

By Cas’s sounds alone, Dean knew his friend loved this. But with his socks and the angle he couldn’t quite get the momentum he needed to make it even better. Knowing he needed a little more he shifted onto his back pulling Cas with him until Cas’s back was solid against his chest. Automatically Cas spread his legs wider giving Dean the space he needed to drive into Cas’s willing body. 

When Cas’s back arched into the new sensations and a guttural moan emanated from his body, Dean lost himself. He drove in faster than he had before, needing to hear those sounds again and Cas didn’t disappoint. 

Over and over his friend whined out his name until Dean felt like he was on the brink—too soon. He wasn’t ready to be done. 

He slowed his pace, eliciting a protest from the man atop him. 

“Roll over—wanna get behind you.” 

Like a fucking cat, Cas rolled over to his stomach and spread his knees wide as Dean moved behind him. It was obscene how Cas pressed his ass back, seeking Dean’s cock almost wantonly. Wanting to last a little longer and in doing so needing to give his dick a little bit of a break, Dean’s thumb pressed against Cas’s hole watching the way it quivered in anticipation. 

“Dean, please!” 

“Fuck, you look good.” 

“_Dean!_” 

He wanted to shove back in and really let loose but with his thumb pressing into Cas’s ass he knew there was a little too much friction of be comfortable. He should’ve been more thoughtful in actually going and getting the lube but he was too pent up with want to be able to stop touching the beautiful man before him. He had to make due. 

As much as he wanted to give in to some certain fantasies he’d been having that involved lubricating Cas’s hole—he didn’t think he had the courage… not yet anyway. Still, it was probably the most debauched he’d done in bed as he dipped his head low enough to let his own spit dribble over the tight ring of muscle and pushed his finger back in to ease the way. 

“Oh god… Dean.” 

“You look so sexy right now.” 

“Please, please, please. More.” 

“Give me a second, baby.” 

He let himself catch his breath for a few moments before he himself was too impatient to feel Cas engulfing him again. Slowly, once more, he pressed back in, plastering his front to Cas’s back and breathing heavily in his friend’s ear. “How do you want it?” 

Cas lowered himself onto his chest and arched his back. “Like this. Don’t hold back. _Please._”

And how could he deny him what they both wanted? 

He gave in to their needs—slammed his hips forward and pulled back, repeating the action until he could feel it down to his toes. He stayed pressed up against Cas’s back, giving in to his desire to bite a few small marks against the back of his shoulder and neck. It was all he could do to keep himself from spewing every thought he’d ever had, everything he’d ever wanted to say to Cas about how he made Dean feel. 

He was too worked up to last much longer and Cas wasn’t far behind if the unrelenting grinding he was doing into the bed was any indication. Dean lifted off Cas just enough for the other man to snake his hand between himself and the bed and then Cas was off like a light—shuddering through his release with Dean’s name on his lips. 

It was moments later that Dean’s orgasm nearly caught him off guard; he had hardly seconds to pull out before he spilled all over the rounds of Cas’s ass—his limbs actually trembling with the effort it took him to not collapse onto Cas’s limp body. 

He let himself fall to the side, giving himself a few moments before he had to crawl out of bed and clean the two of them up. 

Cas’s forehead slumped onto Dean’s shoulder as he too tried to catch his breath. 

At that moment Dean wanted nothing more than to pull him close and kiss him gently, savor the moment as softly as he could after the thrill of their rendezvous. But knowing that it wouldn’t be welcome, he settled with running his hand over Cas’s back comfortingly. 

Later after they were cleaned up and warm under the covers, Dean lay with Cas’s head on his shoulders and finally allowed his mind to sift through the thoughts and feelings he’d had coursing through him all night. It wasn’t the first time those things had popped into his head—kissing Cas, being with him as more than just friends, experimenting more sexually—but this was the first time he hadn’t just pushed them to the back of his mind. It scared him to accept that this wasn’t just about helping Cas anymore. 

It was so much easier when everything was black and white. Sex to teach Cas how to be confident and just being best friends clearly couldn’t be mutually exclusive no matter what Dean had thought at the beginning. Maybe it could have been easier if he hadn’t insisted on holding Cas after every time yet, nothing in him could justify letting his friend go back to a separate bed and deal with all the post-sex hormones alone, especially with his first sexual experience ever. 

Even now, after a few months of this, Dean wouldn’t be able to let him go. Maybe Cas didn’t need to share these moments, but Dean did. He didn’t know at the start of all this how much he’d end up needing Cas. He didn’t need the sex, as amazing as it was, but he needed the closeness, the trust that flowed between them, the way he felt comfortable enough with Cas to be who he wanted to be—in bed or outside of it—and never feeling the need to put on his facade. 

Somehow, his best friend made him feel desired as he was, even if Cas didn’t feel anything towards him romantically. 

Dean’s heart ached, not knowing what he should do. He didn’t think he could end what they had since the selfish part of him couldn’t fathom being without Cas anymore, yet he didn’t know if he could keep doing what they were doing with no security in Cas ever feeling the same way in return. 

All he could do was hope upon hope that somehow Cas would start to want more—that he’d ask Dean to be more intimate, to cross those invisible lines that were somehow drawn without either of them knowing. 

Maybe he’d be lucky and he could have this all for real. 

He hadn’t noticed just how long he’d been lying awake until Cas started to stir at his side. A quick glace to the clock in the room showed that it was nearly dawn and he’d been lying there for hours. 

Cas must’ve noticed his wakefulness because he stretched into a yawn and snuffled back into Dean’s chest. “My thighs are sore.” 

“From the sex or the dancing?” Dean asked through a huff of laughter. 

“The dancing.” Cas confirmed through another yawn. “I think my thighs are used to the sex... vigorous sex.” 

He thought back to a few hours ago and worried he’d taken it too far. “Am… am I too rough with you?” 

“What?” Cas took a moment to blink up at him, eyes adjusting to the still dim light. “No. Not too rough. You—I think… I think you could be a little rougher sometimes.” 

Dean couldn’t be sure but he thought Cas might be blushing or just too tired to really process what he was saying. “Yeah? Is that something you’d like?” 

“I’d like to try it.” 

Dean nodded, “Okay.” He wanted to ask what else Cas might want to try—if there were any other things he felt they could test out together but he was interrupted. 

“More sleep now.” His friend announced, turning over in the bed to face away from Dean. 

His heart twisted a little thinking Cas was kicking him out of bed. He didn’t really know what to do besides ask at this point even though he figured he already knew the answer. He was already moving to slide out of bed as he asked, “Do—do you want me to go to my bed?” 

It was a firm grip to his wrist that kept him from going anywhere but the small, sleepy, “No. Stay,” had Dean falling back into bed and wrapping his arms around Cas and sinking into the comfort of being right where he longed to stay.

**Notes for the Chapter:**

> I'm sorry I never replied back to the comments I received on the last chapter, I hate not replying to everyone but the holidays are a busy, busy time. I do appreciate them and am always blown away by people actually enjoying anything I write. So thank you all times a million! 
> 
> I hope you liked this one <3


	13. December 7, 2017

Finals crept up on them and before Cas knew it, he was spending the majority of his time at the library attempting to study for all the classes he had exams for. As much as he hated being out of their shared room, Castiel had long since learned that Dean was too much of a distraction even before they’d started having sex. 

Dean’s brain worked much differently to his, needing constant breaks in order to retain information, which meant every fifteen to twenty minutes of work equated to an online video or going back to chatting. It was amusing at some points but not when Cas had important papers to finish or a test worth the majority of his grade to cram for. 

And lately, studying with Dean had turned rather… impossible. With the ‘innocent’ groping Dean tried to get away with or the sudden ‘unexpected’ nakedness he’d suffer from, there was no way for Cas to stay concentrated. 

That’s why he was now with Hannah, who didn’t distract him nearly as much as his roommate, in the library sifting through the textbook that he’d notated to death already. He’d never get his money back on this one after the semester was out but if he aced that final it would all be worth it. 

They studied for a while together, Castiel steadfastly ignoring each and every one of Dean’s texts, until eventually Hannah’s attention span tapped out. It was then that Castiel allowed himself to step back from the studying and eat the lunch that she’d packed for the two of them. 

“Are you excited to go back home?” Hannah asked around a mouthful of salad—it was amusing that he was one of the few people his friend didn’t act so proper around. 

Cas thought about her question but only felt morose when he remembered that Dean would be leaving in a few days and Cas had to stay put another week. (Really, what kind of professor willingly chose to host a final on the last Friday before break? He was 99.9 percent sure that this professor was actually a demon). 

Aside from being alone in their dorm for almost a week, Castiel knew that he’d at least be seeing his dad soon. It’d been too long since he’d seen him and that was the one thing keeping his spirits up. 

“I guess I am. I’m excited to see my dad.” 

“It’ll be weird though I bet.” 

“Why?” 

Hannah shoved another mouthful of food into her mouth and took a moment to chew before answering. “You spent Christmas with Dean last year. It’ll probably just be weird that it’s just you and your dad again. You liked going back with Dean.” 

“I did.” Cas agreed, thinking back to his time with Dean’s family. It’d been a loud and sarcastic affair but he’d felt right at home with them all, mostly. “I wished my dad could have been there though. Dean’s family is wonderful but it was strange not having him there with me for the holidays. I’d want him there next time if I ever got invited again… if that were possible.” 

“Did you ask Dean to come back with you?” 

“Oh no. He wouldn’t. Christmas with his family is too important to him.” 

“You don’t think he’d go back with you, not even once?” 

He stopped to think about his friend coming to California with him for a change, bringing him around the places Castiel grew up visiting, spending Christmas with just his dad and Dean… He thought that it’d be nice, great even, but he knew how much Dean loved being with all of his family. 

“I don’t know,” he replied. “I wouldn’t ever ask though. You know Dean, he’d probably feel too bad to say no so he’d go with me just to be kind. I wouldn’t want to keep him from his family. That’s where he truly wants to be for the holidays.” 

Hannah didn’t look entirely convinced but she didn’t seem keen on voicing her thoughts. 

“Maybe,” she said with a shrug, taking another bite of her food. “What about your mystery guy? What’s he doing for Christmas?” 

“Oh, uh—” Cas coughed awkwardly. “He’s… he’s going to his family’s house.” 

“Did he ask you to tag along?” 

“Oh—oh no. No, that’s not—we’re not like—we don’t do stuff like that. It’s just, it’s just a physical relationship. You know this.” 

“Right sorry.” 

Desperately wanting to get away from the topic of his ‘mystery’ man, Cas turned the conversation around on her. 

“Wait, you haven’t told me what you’re doing.” 

“Probably just staying here,” she shrugged. “I told you my mom and dad are going on a cruise, right? They wanted me to go too but no. I’ve seen Titanic. Not for me. When they’re back they said they’ll come here for New Years and get a hotel at one of the casinos for us.” 

“You’re just going to stay here? Hannah, why didn’t you tell me? You should come back with me.” 

“Oh no. That’s okay. I know a few people who are staying here for break so it won’t be a big deal.” 

“I think Dean mentioned that Benny’s staying here too.” 

“Oh? Oh—I didn’t know that. Why would I know that? Obviously I didn’t.” 

It was becoming more usual to see Hannah acting so, _unusual_ yet Castiel still couldn’t manage to put his finger on it. He leveled her with a stare that made her understand he thought she was acting strange. 

“Right…” He said, drawing out the syllable. 

Hannah however ignored him, switching conversation quickly. 

“Have you gone shopping yet?” 

At the words Cas’s mind was a-flurry with all he still needed to get done for the holidays. 

“No. Can we go? I need your help thinking of a few things.” 

“Of course,” she replied. “Let’s go right now?” 

“Perfect.” 

Spending the day shopping with his friend, he realized how little time he’d made for her the past couple of months. In the few years they’d been close it was common for Castiel to see her nearly every day but definitely more than one time a week. Now, he felt that a few weeks would pass without him seeing her. He figured it mostly had to do with being in the “honeymoon” stage with Dean but also just the consequences of growing up. 

It felt good to catch up and hear about the things that’d been happening in her day-to-day life and the drama her roommate kept causing. They laughed as they picked out gifts for certain people and she helped Cas figure out what to finally get Dean that wasn’t the ‘practical’ belt, flannel, or new shirts he’d taken to getting his roommate the past few years Dean needed them, so how could those not be good gifts?

They ventured into a vintage antique store that sold a hodgepodge of items and Castiel found four old movie posters that he knew Gabriel would love and he secretly found a few antique broaches for Hannah since he knew she kept a collection of them. The two of them made another stop at Walmart to grab gift wrapping followed by one last stop to get frozen yogurt before they were shopped out.

Cas’s feet were aching as he shuffled into his and Dean’s room with his arms full of bags. 

Hearing the TV on, Cas knew Dean was still home and attempted to make a beeline straight for the closet to hide the gifts, especially Dean’s. 

“Whatcha got there,” Dean asked with suspicious interest. Cas just knew in his gut Dean was the type who shook all his presents on Christmas morning before anyone woke up. He’d even wager that Dean still did that even as a twenty-one-year-old man. 

“Uh uh. No peaking,” Cas commanded, using his body as a shield while trying to stuff the bags into the already full close. “I mean it!” 

“Oh come on! Not even everyone else’s presents?” Dean whined. 

“No.” 

“Scrooge.” 

“You suck at keeping secrets Dean, and you know it. You let it slip two years in a row what I got for Hannah.” 

He stared at Dean with an unrelenting face and watched his best friend grow a huge pouty lip. _Such a child,_ Cas thought. 

“Fine.” 

“Don’t pout. It doesn’t suit you.” 

“I think I’m adorable.” 

“You’d be the only one,” Cas replied, obviously lying. He spotted the open textbooks on Dean’s desk as he walked over towards the couch. “Are you ready for your final?” he asked. 

“Ready as I’m gonna be,” Dean shrugged, flopping down right next to Cas so their thighs were touching. “How ‘bout you?” 

“Same. I mean, I’m reasonably certain I’ll pass but I’m kind of systems overload right now.” 

“Then let’s just have a chill night. No more studying. Just me, you, and Netflix.” 

“I’m amiable to that.” 

“Nerd.” 

Choosing the futon over the couch often had its benefits, especially that night. It wasn’t the first time he’d picked sitting next to Dean over sitting alone on his bean bag, and it definitely wouldn’t be the last. Especially when halfway through their Netflix binging Cas let his hand wander just enough to grope his friend over the top of his sweatpants, and from there, he managed to give Dean one of the best hand jobs he’d ever given. 

It was falling asleep, spooned by his best friend, that Castiel loved most. 

Waking up the next morning to the sound of their alarms, reminding them of their upcoming finals, was not something Cas loved. 

Testing days were one of the few times in Cas’s life he felt he could be considered a morning person. Too often growing up he’d have nightmares of oversleeping and doing poorly on an exam so he made sure that would never actually come to pass. As much as he wanted to stay in the warm confines of Dean’s arms, he didn’t want to run the risk of falling back asleep. He sat up and stretched widely before slipping out of bed and heading to the shower. 

By the time he was out, towel wrapped around his waist and water droplets still dotting his shoulders, Dean had finally made it out of bed. He was looking at Cas with a sultry grin. 

“What is it?” Cas asked, maneuvering around where Dean was attempting to block the short hallway from their bathroom to their living space. 

“Cas. Pre-test sex,” the other man said as if he’d just invented sliced bread. Cas looked at him with scrutiny, wondering if his friend was serious. They each had an exam in a little over an hour and Dean wanted to have sex? 

He rolled his eyes, deciding Dean wasn’t serious. 

“Pre-test sex isn’t a thing.” 

“Its not?” Dean’s voice was mocking but playful. “Are you sure? I think it’s a thing.” 

Not indulging in his friend’s shenanigans, Cas dropped his towel and bent to pull his briefs up when warm hands gripped the rounds of his ass. 

“Don’t you wanna unwind?” Dean asked, still palming Cas’s ass. “Get all those pre-test jitters out?” 

Slowly Cas pulled himself to a standing position, ditching the underwear he’d just been about to put on. Dean’s hands slid to his belly as the taller man plastered his body against Cas’s backside. Through the front of Dean’s boxers Cas had no trouble feeling his erection pressing against him. 

So, Dean was serious and Cas was torn. 

He always wanted Dean but a part of him worried that he’d somehow forget all about his test and fail the class. 

But Dean took schooling seriously too. Surely he wouldn’t set them both up for literal failure, right? 

“Come on, Cas. I know you wanna,” Dean pleaded in his ear, letting the playfulness in his tone give Cas the choice to say no if he really wanted to. 

“You just want me to suck your dick,” Cas joked, knowing he was going to give in to his base desires. 

Dean’s hips rolled against his backside making his stomach swoop. 

“No, I want you to ride my dick,” Dean rasped, “but I wouldn’t be mad at a little suckage.” 

“That’s not a word.” 

“Good thing you’re the language guy.” 

_To hell with his finals,_ Cas thought to himself, knowing it could be a risky move on both their parts but really wanting to do something with his rapidly hardening dick more than he wanted to get ready for a test. 

“Take your boxers off,” Cas commanded, turning around to face his friend. Dean looked up towards the ceiling with a blissed-out look already. 

“Oh fuck yeah.” 

It took Dean hardly any time at all to have his boxers off and Cas was on his knees just as fast. There was something in the way Dean looked at him when Cas was like this that made him want to always do this for his friend. He relished in the hunger that reflected in those green eyes and the delicious words that fell from that mouth, telling Cas how good he looked like this. 

As fun as it would be to spend a while working Dean up, Castiel still did remember they had somewhere to be soon, so he didn’t wait for an invitation before taking Dean’s cock in his mouth and sucking hard. 

It was just long enough to get Dean really wet before Cas popped off, licking around the crown just to hear Dean moan, before he stood up on wobbly legs and moved over to the couch where he found the lube. 

As much as he wanted Dean’s fingers in him, his friend always took his sweet time opening him up and Cas was too pent up already to wait longer than he needed to. With his knees planted on the couch cushions and his arm bracing against the back of the futon, he worked his hand behind himself slid a finger in—possibly arching his back a little too much to give Dean a bit of a show. 

He may have been overzealous in taking two so soon, but with Dean next to him on the couch, staring at him like he could eat Cas alive, there was no way Cas wasn’t going to get on his dick as soon as possible. 

He clambered a little awkwardly until he was straddling Dean’s thighs and bracing himself on the back of the couch, bracketing Dean in between his arms as the other man lined his cock up with Cas’s newly wet hole. 

With an exhale Cas sank down, just enough to get Dean inside him before he circled his hips and willed himself to relax enough to sink down further. 

Their shared groan as Dean slipped further in his ass had Cas’s eyes fluttering. 

Already this was amazing but riding Dean’s dick on their too small couch, it checked off a box of Cas’s fantasies he hadn’t been able to voice yet. 

Maybe someday he’d be able to ask Dean for what he wanted, it was something he still struggled with in their arrangement, but if Dean somehow figured out more of Cas’s secret fantasies, well Cas didn’t see a problem with that. 

His hips steadily moved at their own accord now, no longer unsure of the rhythm he needed to keep. No, now he knew what felt good and what made Dean’s fingers tighten around his hips. Now Cas didn’t have to overthink what would bring them the most pleasure because his body could just respond to Dean’s so seamlessly. 

Each time they did this, connected their bodies together like this, the same thoughts always flittered through Cas’s mind. _So good. So good. It’s never felt this fucking good before. Fuck._ and _this_ time he really meant it. But he thought every time was the best. Dean was too good. 

Cas’s mind was hazy with lust as his movements started to speed up. He nearly couldn’t remember his own name as he rocked his hips just right, and Dean’s hands soothed up and down his sides. 

Wanting more but not knowing what that more was, he moved so his hands braced on Dean’s thighs and his feet planted on either side of Dean’s hips on the couch cushion. 

That! That was what he wanted. 

Electricity raced down to his toes as his new position reached places he didn’t know needed to be reached but… he needed—he needed more, just a little bit more. He sped up his hips letting the pulsing energy course through him. The current was so strong he almost felt like he was going to melt he just—he just needed. 

Trying to brace himself on one hand he attempted to grip his own cock but he couldn’t—he couldn’t without losing this feeling. 

Every part of him felt awake but so overwhelmed, he didn’t even notice he was mumbling, “I can’t—I can’t—I need…” over and over. 

He didn’t know if Dean was feeling this too, he could hear his friend saying something—he thought he heard him say how sexy Cas was…. He loved when Dean said that. He loved when Dean told him he looked good. And when—and when Dean called him baby… the first time he called him baby it made Cas see stars. He wanted to hear that again. 

But he wanted—he wanted more now. 

“Dean!” 

Dean’s hands on his hips helped him speed up but it wasn’t enough. He was so close. Just a little more—

He tried again. He tried so hard to get his hand on himself but he couldn’t without moving and he needed it like this... _just_ like this. 

Maybe he whined. Maybe he begged. He didn’t know. But he was fully aware of his surroundings when he suddenly felt the most mind-melting feeling ever, his hips stuttering at the shock, only for a moment. 

Dean’s hand was wrapped around Cas’s length and stroking him in sync to Cas’s hips. 

He never knew he could moan so loud, nor mumble such incoherency and Dean… Dean didn’t stop. Lord above, he didn’t stop. 

Cas might’ve sobbed as he came or he might’ve screamed—he wasn’t sure but the electricity still coursed through him as he slumped down into the couch as he came down from such a high. 

“Holy shit.” 

He almost thought he’d said that until he cracked open his eyes and saw Dean staring down at him from his spot on the couch. 

Dean was hovering above him, looking down at Cas with flushed cheeks and wide eyes. Catching movement, Cas trailed his eyes down Dean’s body to where Dean now had his own cock in hand and was slowly stroking it as he stared down at Cas. 

“Dean… you didn’t come?” Cas asked worriedly, not knowing what he did wrong. Dean never came in him but he always came right after he pulled out. 

“Not yet,” the other man panted, his hand beginning to move faster. 

“Do you want me to suck you?” Cas offered, hoping it wasn’t the fact that he’d just jacked Cas off making Dean unable to come quickly. 

“Can I?” Is all Dean asked, but the gaze of his eyes on Cas’s stomach and the speed of his hand was all Cas needed to know. 

“Yeah, come on me,” he encouraged. 

It didn’t take long until Dean’s rapid tugs on his cock made his come spurt out in ropes on Cas’s torso. The words out of his mouth were, “Fuck, baby.” 

Cas was certain he was in heaven. 

Dean dropped down next to Cas, wedging himself between the back of the futon and where Cas was laying on his back—a tight fit no doubt. 

Though the come on his stomach was already starting to cool and he had no clue when he needed to head to his class, Cas’s limbs had checked out for the day. 

“I don’t think I can go to class now,” he mumbled, letting his heavy eyes start to drift shut. He felt Dean laugh into his shoulder before his friend nudged him nearly off the couch. 

“Up you go. Cold shower,” Dean demanded playfully, making Cas whine. 

“No.” 

“You gotta. We have tests.” 

“But I’m jello.” 

“You’ll live.” 

Cas let out a huge yawn right at that moment which, sadly, did not deter Dean from yanking him up to his feet and shoving him towards the shower. 

He showered much quicker this time around and hurriedly dressed once he realized they had less than twenty minutes to get to class. 

As he scrambled to make sure he had pencils and erasers ready and matching shoes on his feet, he hardly noticed Dean getting dressed beside him. It was when Dean pulled out one of their emergency cans of coffee and a Pop Tart and handed it to him that Cas calmed down a fraction. 

“You’re gonna do awesome, dude,” Dean reassured, “You’ve been studying forever and you could do all of this in your sleep.” 

“Thank you. You’re going to do great as well.” 

“I know. Then we can come back here and celebrate?” 

“As long as there’s pizza and beer.” 

“Done and done.” 

Later, as he was walking out of the lecture hall, Cas wondered if Dean had been onto something about pre-test sex because as far as he could remember, Cas had never felt as confident in his testing as he had during that particular final.

* * *

The last few days of the semester crept up on him and before he knew it, he was watching Dean pack for the holidays. 

He was feeling mixed about going home. As much as he wanted to see his dad and spend the holidays with him like they used to, the thought of being away from Dean for nearly a month dampened his excitement. 

The self-doubt didn’t help his situation either. 

As much as Cas wanted to believe that after break the two of them would pick right up where they left off, he worried that Dean would leave and realize just how much time he’d been wasting with Cas when the other man could have anyone he wanted. 

What if Dean met someone over break? What if he wanted to be in a relationship with her and then Cas and Dean’s arrangement completely disappeared? His heart broke just thinking about it. He wanted to keep Dean as long as possible but he didn’t have high hopes for being able to manage it. A month apart would surely be the end to this and there was nothing he could do. 

Even Dean seemed a little down or maybe it was just a fluke, but for a man who often looked like a kid on Christmas, Dean seemed more morose than usual packing his belongings. Where Cas was used to watching his friend practically topple the dresser into his bag in excitement, Dean was now methodically folding his clothes, placing them in the bag, taking them out, switching them for something else before repeating the process. 

“Are you okay?” Cas asked, pulling Dean from his trance. 

“What?” Dean looked up shocked, “Oh, yeah. I’m good. Just thinking.” 

“About?” 

“Just… it’s weird isn’t it?” 

“What is?” 

“This is our last winter break of college. We have one more semester after this and then we’re done.” The thoughts seemed to really trouble Dean which took Cas aback. 

Dean had always been eager to finish with schooling and go on to the next chapter in life. Especially when graduation meant that Dean got to be close to his brother again. 

“I thought you were excited to graduate?” 

“I am but… what happens after?” Dean’s eyes strained at the corners. Cas could tell these thoughts were really plaguing him. 

“What do you mean?” 

“I just keep thinking that everything is going to change. None of us are going to see each other like we do now. What if we all don’t stay in touch.” Cas frowned deeply at Deans’ words because they were his fears too. “What if me and you lose touch? I just—I don’t want anything to change.” 

“They won’t,” Cas quickly insisted, if not for Dean, for himself. 

“How do you know?” 

“Because I don’t want anything to change either. If we both don’t want to lose touch then we’ll make sure that happens. That goes for everyone else as well.” 

“Cas, everyone _always_ says they’re going to stay in touch but then they never do.” 

Deep down he knew what Dean said was true. Most people did lose touch after graduating. Heck, he’d lost touch with some of the people he swore to not lose touch with from high school but that had to be different. He didn’t spend nearly every waking moment with those people. He didn’t confide his entire life story, all his thoughts and fears, and his deepest secrets to those people. Hannah, Benny, Sam, Dean—they were all people he couldn’t imagine never having in his life again. 

“I worry too, I worry about it a lot actually but we can be different.” 

Dean looked over at him hopefully. 

“How?” 

“Promise me.” 

He watched Dean’s eyebrows scrunch together. “What?” 

It felt silly, like a childhood promise but Cas decided to say it nonetheless. 

“Promise me you won’t lose touch with me after we graduate.” He stared at Dean expectantly, knowing his friend probably though he was acting silly. 

“You’re serious?” 

“Of course I am,” Cas confessed, smiling. “You never break your promises.” 

Though he was trying to keep it lighthearted, his request for the promise was genuine. Dean never broke his promises and Castiel liked to think he wasn’t the type of person to break his own promises either. Maybe his intent came across to Dean or maybe Dean was just as desperate for some sort of reassurance that he nodded in agreement. 

“Fine, but only if you make it too.” 

“Deal.” 

A faint red tint colored Dean’s cheek as he said, “I promise I won’t lose touch with you after graduation.” 

Cas tried to bite back the exceedingly pleased grin pressing at his cheeks but he knew he failed. He reached his pinky out towards his best friend as he stated in return, “And I promise I won’t lose touch with you either.” 

Dean’s pinky wrapped around his with might, and Cas could almost feel the relief the other boy felt from the gesture. 

“You think we’re stubborn enough to keep these promises?” Dean asked, only then slowly releasing his grip. 

“I know we are,” Cas insisted. 

He wanted so badly to pull Dean into a hug and tell him that if he had it his way, he’d keep Dean in his life forever, right by his side. He wanted to tell Dean not to go back home and to go back to California with him so they wouldn’t have to spend four long weeks apart and he could show Dean the places he used to go when he was in high school—just like Dean had done for him last year. 

Instead, he helped Dean finish packing up the rest of his things before suddenly remembering the packages he’d hidden in the back of their closet. 

He rushed to get them before Dean zipped up his bag. 

“Oh, Dean, I almost forgot. Don’t forget to pack these.” He said as he handed Dean four wrapped gifts. 

“What’s all this?” 

“This is for you,” he handed Dean his package before handing over the other three, “and these are for Sam, Bobby, and Jody.” 

“Cas… you didn’t have to get them anything.” 

The fact that Dean looked genuinely touched that Cas had gotten his family anything told Cas that he’d made the right call. He didn’t break the bank or anything but he hoped they would all appreciate the gifts. 

“I know, but I wanted to,” He admitted. “They welcomed me into their home last year and… they were so kind. I just, I wanted to get them something too.” 

For some reason, Dean stared at him for a little while before shaking his head and grabbed something out of his sock drawer. 

“I—I got you this,” he mumbled, handing Cas a horrifically wrapped present. The fact that Cas knew Dean had taken the time to even try wrapping it himself made his chest fill with too much warmth. 

“Thank you,” he barely managed to whisper. 

“Do you—should we open them together now?” Dean asked. 

As much as Cas wanted to see Dean’s face when he opened his present, Cas also knew what was in the box. He’d seen the wood face watch with the leather band and had immediately thought about how attractive it’d look on Dean’s wrist. The price wasn’t really in the range he and Dean silently seemed to have agreed on in the past, but he knew his friend would immediately think it too much and insist Cas took it back. Wanting to someday see that watch on Dean’s wrist, he knew it was best to make Dean open the first when he was states away and couldn’t refuse it. 

“Maybe we should wait until Christmas?” He suggested, hoping Dean didn’t question him. 

“Yeah, yeah, we can wait.” Dean pouted. He always did love opening gifts. 

Cas watched his friend patter around the room for a little bit before huffing and declaring, “Okay, well I better get going.” 

A protest fought its way towards Cas’s lips but he swallowed it down, rising to his feet as Dean shouldered his duffle. 

“Right. Are you sure you’ll be good to drive the whole way?” 

Dean gifted him an easy smile. “I’ll probably stop in Colorado and crash there for a night then finish off.” 

“Wouldn’t flying be easier?” Cas couldn’t really fight back the worry of Dean taking this car trip alone, even though he knew Dean was an excellent driver. 

“You saw me last year on that flight, man. They’re the worst.” 

“Just—just let me know when you arrive safely.” He phrased it like a question but knew Dean could see right through it. If he didn’t hear back from Dean within a timely manner, there was no doubt he’d be calling his friend frantically until he picked up. 

“Promise.” 

“And don’t drive until you’re exhausted.” 

“If I didn’t know better I’d think you and my mom were teaming up on me.” 

Dean’s smile was bright as he backed up towards the door. Cas knew his friend was only teasing him but he felt a little silly for being so worried. 

“Sorry—it’s not my place,” he tried to apologize but Dean waved him off. 

“No, it’s fine. I was gonna say the same thing to you—with your flight and all. To—to let me know when you get back to Cali safe.” 

“I will,” he promised. 

Dean looked nervous for some reason, scratching the back of his neck as he fumbled to say, “Okay—well uhm, I guess I should—I guess I should get going.” 

And Cas… Cas didn’t want him to go. He really didn’t want to watch Dean walk out that door and nearly listened to every fiber of his being begging him to make Dean stay. But instead he put on a brave face and said, “Right. Of course.” 

“I—uh—I’ll see you in a month then.” 

“Yes. You will. I’ll see you then.” 

And he could have just said bye there and let Dean walk out the door but he couldn’t. Instead he heard himself say, “Actually, how about I walk you to your car?” 

He might have imagined that Dean smiled, just a little, hearing him say it. 

A chill hit him as he walked towards the parking lot, having left his coat in the dorm. He wrapped his arms around himself as he watched Dean throw his duffle into the back seat. 

“Promise you’ll be safe?” He asked Dean, instead of what he truly wanted to ask him. 

“I swear.” 

“Have a great vacation.” 

“You too Cas.” 

He smiled and nodded and was about to turn away when Dean took a few steps towards him and outstretched his arms. Immediately, Cas curled into the warmth of Dean’s embrace, wrapping his arms around Dean’s shoulders with all his might. He could have stayed like that for hours but he knew he had to let Dean go. Regretfully he pulled back with a small smile, appreciating that Dean promised once more to call him when he got to his first stop. 

He didn’t want to admit it but a part of him felt like tearing up as he watched Dean’s car drive away, but his heart was definitely heavy in his chest. He tried to tell himself that he only had four short weeks until they’d be back together again, but somehow four weeks felt like a lifetime. 

Three hours of wallowing in his loneliness and Cas nearly jumped out of his skin when his phone chimed beside him. He fumbled with it a few times before he was able to unlock it and see Deans’ text. 

**Dean:** I’m at a rest stop and they’re all out of monsters

He could easily imagine Dean grumbling and pouting about his lack of energy drinks. He smiled at the thought. 

_Cas:_ Good riddance! That stuff is poison! 

**Dean:** It’s essential to my survival. 

_Cas:_ What ever will you do? 

**Dean:** I guess dr pepper will be enough 

_Cas:_ Knowing you you’re buying no less than three. I think that’ll do it. 

He waited for a little while for a reply but when he got one, he assumed Dean was back on the road. 

Feeling a little happier that Dean had in fact told him when he made his first stop, Cas settled back down on the couch to watch TV, hoping he’d hear from Dean before he headed to bed that night. 

Cas was still on the couch later night, completed sprawled out in his laze when his phone buzzed again. 

**Dean:** Just got to a motel. 

**Dean:** Just wanted to let you know. 

_Cas:_ I’m glad you’re safe. How was the ride so far?” 

**Dean:** Boring. I didn’t realize how much easier it in to drive with someone else in the car. Even I’m getting sick of my own music. 

_Cas:_ Is that even possible? 

**Dean:** I didn’t think so until now.

**Dean:** What’re you doing?

_Cas:_ Just watching TV. Nothing too exciting on my end either. 

**Dean:** You have the whole room to yourself. You could do anything. Walk around naked. Watch porn on the TV. 

_Cas:_ Who said I’m not naked?

**Dean:** Pics or it didn’t happen

_Cas:_ I’ll show you mine if you show me yours. 

**Dean:** tease

**Dean:** I’m going to crash. I didn’t realize driving can wipe you out so much 

_Cas:_ Sleep well. 

**Dean:** Night buddy 

_Cas:_ Goodnight, Dean. 

Cas woke, late the next morning to the sound of his phone pinging again. He checked the time to see it was nearly noon and smiled sleepily realizing it was another update from Dean. 

**Dean:** Made it home!

_Cas:_ Good. I’m glad. Tell your family I say hi. 

He snuggled back down into the warmth of the pillow under his head, reveling in the fact that he’d slept in Dean’s bed that night. It felt like his own little secret—one he justified by telling himself he only did it to be able to watch TV as he fell asleep. But deep down he knew that sleeping without Dean by his side nearly felt impossible these days, and at least having his scent surrounding him made it easier. 

It had only been less than one day and Cas didn’t know how he was going to stand being so far away from his best friend for one whole month.

**Notes for the Chapter:**

> This was one of my favorite chapters to write and I hope you all like it as well. 
> 
> The next chapter should be out next weekend but after that I won't have fully pre-written chapters and might have to slow down with posting weekly (but I will do my best to be quick). I just wanted to give a heads up.


	14. Decemeber 15, 2017

Apparently being back home meant he was back to being the designated household snow shoveler. It had only been four days since he’d been back but this winter was already one of the worst he’d seen, the snow falling way earlier than he’d seen before. 

He missed the desert way too damn much and only wanted to rush back that much more as his shoulders ached from lack of use. He still kept himself fit but the motion of hauling shovels of snow around the yard was killer. 

He was taking a break on the couch as his parents were at work and Sam was still at school for the day. He had a whole other week until Sam would officially be on his school’s break and Dean was _bored._

The cable at the house was currently down and the internet seemed to be running slower than molasses. He was damn near ready to take a nap just to have something to do, when his phone chimed. 

**Cas:** My plane just landed. 

Dean tried to hide his smile seeing Cas’s name on his screen but no one was around to see it anyway. 

They’d been texting almost constantly since Dean had gotten back and he was damn happy about it because he wouldn’t have known what to do with himself if he couldn’t talk to Cas. 

He wrote and deleted a few messages before he settled on: 

_Dean:_ Let me know when you’re with your dad. 

**Cas:** I will

_Dean:_ Glad you’re safe 

**Cas:** Is the cable still out? 

_Dean:_ yup 

**Cas:** Do you want to talk on the phone while I wait for my luggage? 

Reading those words had Dean’s heart fluttering in his chest. He felt like a pre-teen with a crush. 

_Dean:_ course I do 

Within moments his phone was ringing and Dean didn’t even wait a beat before answering. 

“Hey Cas.” 

“Hello, Dean.” 

He wasn’t sure if anyone made him as happy as Cas did. How was it possible that hearing only two words turned Dean’s entire day around? 

“How was your flight?” 

“Not terrible,” Cas replied, a little muffled from the hustle and bustle of the airport in the background. “I sat next to this mom and her five-year-old and he let me share his coloring book the whole time, so that was very nice.” 

Dean smiled at the image. Cas somehow had a way with younger kids. It made Dean wonder what the guy would look like with kids of his own someday… 

“How do kids always love you?” 

“I’m not sure. Maybe it’s because I answer any of their questions outright.” 

“That’s gonna get you into trouble someday,” Dean joked. 

“I like to think I’m smart enough to not forever scar a child with my honesty.” 

He laughed in agreement. God, he already missed his friend so much. 

It seemed to be slightly quieter on the other end of the phone so Dean asked, “You at baggage claim yet?” 

“I just got here. It looks like I walked slow enough that the bags are already coming out.” 

He felt his bottom lip protrude like a child knowing that this meant he’d already have to get off the phone. 

“Want me to let you go?” 

“You don’t have to,” Cas said, sounding a little bummed too but that was probably just Dean’s hopeful thinking. Still, he might not go to airports a lot but he knew baggage claim wasn’t for the weak and it’d be rude to keep Cas on the phone. 

“Yeah but pulling luggage off those things is a two-hand deal. Just text me when you’re with your dad, okay?” 

“I will. 

His heart already felt heavier in his chest but he hoped this wouldn’t be the only time he’d get to hear Cas’s voice during break. “Talk to you in a bit.” 

“You will,” Cas promised. 

He didn’t let Dean down. It seemed like the moment he’d gotten his bags in the car, Dean was receiving a text. Dean laughed at Cas’s play-by-play of his car ride with his dad who was apparently talking a mile a minute about everything Cas had missed since he’d last been home. Cas seemed to think his dad was purposely trying to mess with him but Dean knew Cas was happy to be back with him. 

It made Dean wonder what they’d do if they ever did end up together like Dean hoped. From what Dean knew, Sam still wanted to move to California and Dean was fairly certain that Cas would move back home once they graduated. Was it possible that Dean and Cas could stay close? If they were together, they could maybe even trade off where their families went for the holidays, maybe trade off each year or pick which ones to go to. 

It was too far in the future to really worry about yet, but he hoped that he’d someday get the chance to have to worry about it. 

After a while Cas went silent and Dean assumed he was busy with his dad, so without any messages back, Dean fell asleep on the couch with his phone to his chest, not willing to leave a message from Cas unanswered. 

He was such a teenaged girl, but honestly, he didn’t mind. 

His nap came and went and he was disappointed to see that there wasn’t another new message from Cas. It’s not like he expected Cas to text him at every waking moment, that’d be insane, but without his family members home to distract him, it sucked to not have Cas to talk to either. 

He tossed his phone away from him so he wouldn’t end up bugging his best friend with eight thousand texts, and stared up at the ceiling, hoping the snow would stop holding the cable hostage. 

God, he was _bored!_

The front door opened what felt like two thousand years later to the sound of his little brother calling out, “Dean, you awake?” 

“Yeah, just on the couch,” Dean grumbled. 

He heard Sam’s bag being dropped on the ground and what he thinks was Sam’s shoes being taken off and coat being thrown on the rack. Not long after his brother walked around the couch and stared down at Dean so Dean’s vision of his brother was upside down. 

“You okay?” His brother asked, concerned. 

“Yeah,” Dean shrugged. 

“Are you sure? You look sad.” 

“Just bored. There’s nothing to do,” Dean whined, gesturing to the powered off TV. “Cable is out and the internet hasn’t been working when you guys leave. It’s like you’re your own portable Wifi or something.” 

“Oh crap! I forgot!” Sam’s eyes were wide and he grimaced at Dean like he’d done something wrong. “We turn it off during the day when we’re out to save on power. I usually go through the house and unplug everything. You didn’t check if it was plugged in or not?” 

Dean wanted to shove his brother for not thinking Dean would need cable or internet while he was home alone for _ eight hours!_

“No! I didn’t even _think_ to do that.” 

“Dude, I’m sorry, really. It’s just I’ve been learning in my sustainability club that it helps keep energy costs down when you unplug anything nonvital.” 

He was a little annoyed but he definitely understood. His dorm room had special outlets that turned all their shit off during certain times of the day (he’d learned the hard way not to plug a mini fridge into one of those), so he got the whole save the polar bears thing. It still sucked that he’d been stuck being so bored since his brother forgot people might like entertainment during their winter breaks. 

“Nerd,” he chided, just because he could. Sam ignored him and went back being the TV stand to plug back in the cable box before he sat down on the other couch. 

“Are you sure you’re okay?” 

Dean yawned heartily around his answer, “Yeah, why?” 

“You seem sad? Are things good with you and Cas?” 

God damn it. Sam hadn’t asked about Cas the whole time Dean had been home so far and Dean was naïve to think his brother would have forgotten. 

“Yeah?” 

“You miss him, don’t you?” 

That was an understatement if he’d ever heard one, but his brother didn’t need to know that. 

“Jesus Sam, I didn’t come here for chick flick moments. I’m fine,” he lied. 

“You’re not though. You’ve been staring at your phone since you got here and you mope around when you’re not texting him.” 

All Dean could manage were a few unintelligible sounds of protest, sounds that Sam promptly ignored. 

“Have you talked to him? About how you feel?” 

Dean wanted to bust up laughing because did his brother not know him? Talking about feelings was about as appealing to Dean as eating his own arm—he’d do it if his life depended on it but it wasn’t something he’d just do on his own. And this? His feelings for Cas were a big deal, not something he could just throw out into the world and see what happened. No, he had his entire friendship at stake here. 

“No and I’m not gonna.” 

“What? Why not?” 

“He’d have said something by now no? You’ve met the guy, he always says what’s on his mind. So I just—I don’t think he wants this to be anything more.” 

He’d gone round and round with these thoughts more than he could count. Sometimes he’d even convince himself that Cas might want something with him because it felt so right to lay in each other’s arms, and to pull Cas closer to him in the middle of the night. Sometimes it felt like Cas wanted to just be next to him and to spend all his time with Dean like Dean felt in return. But they’d been doing this for months and for someone who usually says what’s on their mind, there wasn’t a whole lot of “Dean, I want to be with you,” coming out of those perfect lips. 

He tried to explain some of this to his brother, trying to sound mildly optimistic even though he wasn’t really. 

“Maybe someday he’ll realize that he does and all he’ll have to do is ask and I’m his but—I’m not going to keep my hopes up. He’s going to get bored soon and if he says he’s had enough, it’ll be easier to just walk away if I don’t go and gush about how I really fucking like the dude and everything.” 

“But he does like you,” Sam counter argued, looking at Dean with sympathetic puppy-dog eyes. 

“No, you just want him to like me.” 

“I really think he does.” 

“Then why hasn’t he said something?” 

“He’s probably just scared you won’t want him back.” 

It seemed like a joke, because at this point Dean felt like he had a neon sign glowing overhead that said _‘I have a thing for my best friend!’_ He felt like he couldn’t be more obvious at this point, especially when they were having sex. When they were together like that Dean swore his hands couldn’t leave Cas’s body even if he tried because he couldn’t get enough. He couldn’t even help himself anymore from gushing the whole time too, telling Cas just how fucking incredible he always looked like that. God, he’d even started calling Cas ‘baby’ because his stupid heart was so infatuated, he thought it would tumble out of his chest. 

If Cas couldn’t tell just how much Dean wanted him, then he was blind, but Dean knew that his friend was probably just trying to be nice. He’d only gotten in this to learn about sex, he wasn’t looking to find a long-term partner. 

“That’s insane. You were able to figure it out within a few hours,” Dean argued. “How has he not seen how much I want him in the four months we’ve been doing this? He just doesn’t want me back Sammy.” 

“Just tell him Dean. I think you’ll be surprised.” 

He knew his brother wouldn’t let it go so he had to appease the kid someone, even if Dean didn’t really mean it. 

“Maybe. If he gives me a clue he might want this too. Then maybe,” he said dismissively. 

“We’re not done talking about this.” 

“Yippee.” Dean sassed. Thankfully their mom walked through the door announcing they were having takeout for dinner and Dean managed to get away from his brother’s meddling for a little while longer. 

He was in bed that night, squared away in the guest room since Sam had decided he didn’t need two beds in his room since Dean moved out and was rarely back at home. It felt weird to be in the unfamiliar room but he was kinda grateful to not have to have his brother pry into his feelings either. 

Even though it was late, he still wasn’t tired due to his various cat naps that day and found himself on Netflix as his family slept down the hall. 

As soon as he heard his phone chime his chest filled with warm anticipation. 

**Cas:** Are you up? 

Dean bit his lip wondering if Cas knew what texts like that implied, but he thought better of sending his friend a dirty text in response. 

_Dean:_ Yeah why? You okay?

**Cas:** I am. I was just wondering if you wanted to talk. 

_Dean:_ Course I do

**Cas:** :) 

**Cas:** How is your family?

_Dean:_ They’re good. They keep asking about you. Told me to tell you to have a good holiday. 

**Cas:** Tell them I said the same. 

_Dean:_ I will. 

**Cas:** What are you doing right now?

_Dean:_ Laying in bed. Watching Netflix 

**Cas:** Anything interesting?

_Dean:_ Not really. 

_Dean:_ But I can think of something far more entertaining than TV

He was throwing caution to the wind. 

This late at night, alone in his old bedroom, texting the boy he had deep feelings for? The boy he could spend hours worshiping with his mouth if he ever had the chance? The boy who looked so fucking perfect, no matter what he was wearing or wasn’t wearing…. Yeah Dean couldn’t, in good conscience, pass this chance up. 

**Cas:** Yeah? 

Dean couldn’t tell from the tone if Cas was catching on but he’d give it a go anyway. If Cas didn’t like it then they wouldn’t do it again, but this was a part of the sexual experience, wasn’t it? 

_Dean:_ [Attached: 1 Photo] 

The thirty seconds it took Cas to respond felt like hours. 

**Cas:** Are you trying to sext me?

Dean took that response as a good sign. Since Cas didn’t ask him why he’d done that, or tell Dean to not do it… it had to mean he liked it, right? 

_Dean:_ Is it working? 

**Cas:** [Attached: 1 Video]

**Cas:** Perhaps 

Dean’s hand was trembling as he clicked play on the short video—a shaky camera angled down at Cas’s groin where he was rubbing himself on top of his basketball shorts. 

_Dean:_ Fuck

_Dean:_ you wanna do this? 

**Cas:** Please 

_Dean:_ take off your pants 

**Cas:** I did 

_Dean:_ I want pics for proof 

**Cas:** [Attached: 1 image] 

Dean tried to stifle his groan, forgetting that he wasn’t back at the dorm where he didn’t have to worry about sound carrying from room to room. Fuck, that image alone would get Dean through the rest of these weeks without his man. 

_Dean:_ good 

_Dean:_ lube? 

**Cas:** yes 

_Dean:_ get yourself wet baby and let me see 

**Cas:** [Attached: 1 Video] 

_Dean:_ that’s so fuckin hot 

**Cas:** wanna see yours 

He was hoping Cas would ask. 

With no shame Dean took a few pictures of his aching cock, sending one with it laying against his belly and another of his hand wrapped around the base of it. 

**Cas:** I want to see you touch 

**Cas:** please 

Dean wished he could let Cas hear his thoughts as he stroked himself with his camera capturing every movement. He wished Cas could know that he was thinking of his friend’s hand on him. 

He knew Cas would be able to hear his panting but he wasn’t sure if his friend could hear his choked-off _‘Cas’_ as he came all over himself. 

It was undeniable though when he got a video in return when Cas moaned Dean’s name, just as he always did, right as he came. 

Dean saved all the pictures and videos because he knew he wouldn’t be able to get enough of looking at them. Not now and not ever. Cas was perfect, in every way Dean could think of. 

_Dean:_ damn 

**Cas:** My sentiments as well. 

_Dean:_ Is it okay that I saved those? 

**Cas:** You did? 

He wasn’t sure if Cas was pleased by that or not but he hoped his friend wouldn’t ask him to delete them. Not yet at least. 

_Dean:_ ya it was hot 

**Cas:** Can I save yours as well? 

_Dean:_ hell ya 

Knowing that Cas might open those pictures of him later and use them to his liking… it did things to Dean’s insides. He just hoped Cas knew there was more where that came from. 

He closed his eyes and imagined hearing Cas’s voice over the phone as Dean instructed him what to do to himself. They should definitely try phone sex too. 

But for now this was a good start. 

_Dean:_ but we can do that again whenever you want 

**Cas:** I’ll hold you to it. 

**Cas:** I think I’m going to fall asleep soon. 

**Cas:** I hope you’re having a great break so far. 

_Dean:_ You too Cas 

**Cas:** Goodnight, Dean 

He didn’t know what possessed him to do it but before he could chicken out, he pressed send. 

_Dean:_ night baby ;) 

**Cas:** :) 

That night Dean fell asleep with a smile on his face, wondering if Cas was lying in bed thinking of him too. Did Cas wish they were wrapped up around each other? Did he miss the feeling of Dean pressed against him like Dean was missing Cas? 

Dean can’t even remember the last time he hadn’t had Cas in his arms after an orgasm. It was a feeling he really didn’t want to get used too, being away from Cas after such an amazing sensation. Cas was supposed to be there, warm and sated beside him, breathing against Dean’s neck in the most perfect way, lulling Dean to sleep with the comfort of knowing his favorite person was by his side. 

His dreams were great that night, even if his bed felt a little too large and a little too cold.

* * *

He’s already been at home long enough that Christmas was two days away. The presents under the tree that had his name on them were taunting him and Dean was really feeling the Christmas spirit. 

He was significantly less bored now that Sam was officially on his school’s winter break and both Jody and Bobby had been able to take a few days off here and there to hang out with him. He hadn’t really known just how deeply he’d been missing his family until he finally got to spend time with them to his heart’s content. 

He’d nearly forgotten how funny Bobby was when he complained about some of his workers. He’d also forgotten how comforting it was when his mom would scratch his back with her nails and she passed him in the mornings, her silent little hello before she had her coffee. 

He loved these people more than he’d ever know how to express and he wanted to bottle this feeling up and take it with him everywhere he went. 

To him there was only one piece missing that would make everything picture perfect and he spent way too much of his free time fantasizing about it. If next year he could bring Cas home as something much more than a friend, introduce him to the people he cared for as something _more,_ how much more perfect could it get? 

But those fantasies came with one burning question: what would his parents think? 

Would they be happy for him? Would they be disappointed that he’d gone and fallen for a boy? Even if they said before that they adored Cas? Was there a side to his parents that he’d never known, one that hated people who loved the “wrong” person? 

The thoughts gnawed at him until he had to find out. 

“Hey, mom—I uh. I have a weird question.” 

They were standing at the kitchen island with all the ingredients out to make chocolate chip cookies. His mom had on her R2D2 apron Dean had gotten her a few birthdays ago and she was hardly paying much attention to the fact that Dean was shifting around like kid caught red-handed. 

“Okay?” 

“It’s uh. It’s a hypothetical one because I was watching this uh—I was watching a movie where a kid he uh he told something to his parents and they didn’t react so well so it made me wonder if that kid was me how you and dad would react and I was just uh wondering.” 

Already he knew this was a train wreck but he was going to power through, no matter how it turned out. 

He now had his mom’s full attention as she looked at him with confusion in her eyes. 

“I’m not following.” 

Dean swallowed and tried to lean himself against the island to keep his knees from buckling. 

“Uh—say… say that I came home one day and I told you that I wasn’t exactly how I thought I was. That I uh. That I liked things that I use to think I didn’t like.” 

“Are you trying to tell me you now like vegetables or something?” She was smirking at him like she was thoroughly amused by his yammering. 

“Uh no. I just—” He tried to take a soothing breath but it came out shaky and loud. He could feel his mouth become rapidly drier the more he tried to swallow. With another weak breath he tried to speak again. “The kid in the movie he uh, he came out to his parents as… as gay and I was thinking, like, what would you or Bobby say if, like, me or even Sam said that we liked guys but we still liked girls too but we might be interested in a guy and… I just, I just thought I’d want to know what you’d say if I said something like that…” 

It’d all came out in a rush and his heart was hammering in his chest and he considered throwing up, but as the words tumbled past his lips he realized how stupid he sounded and his mom must’ve thought so too as she said his name for the third time. 

“Dean?” 

“No. Sorry. That was stupid,” he waved off, hoping that she’d just drop it. “Of course you wouldn’t care. You’re both practically saints. I just thought maybe…” 

He stopped short for a moment realize he didn’t want her to drop it. The mere idea that her or Bobby could be disappointed in him for having romantic feelings for a boy… it made him sick. He just had to know. 

“Maybe I just want to hear it out loud? That you wouldn’t hate me…. Or Sam… if we said something like that to you.” 

He had her full attention now, though he couldn’t quite meet her eye. He was too scared to know. 

“If—and this I assume is still all hypothetical?” She asked clarifyingly. 

“It is.” 

It was quiet in the kitchen for a while and Dean really thought he was at risk to pass out. Then mercifully she started to answer him, soothing all the fear he’d had moments ago. 

“If one of you came home and told me that you may have feelings for both guys and girls, then I would say that I am extremely fortunate to have a child who is so open to love that they would not shut down any form of it if it came their way. That I would be proud to call them my child and that I would hope that they could bring home whomever it is that they chose to let into their heart.” 

He’d forever deny that tears flooded to the edges of his vision as relief swept right through him. He knew he’d gotten lucky when she chose him and Sam… when she didn’t have to keep such broken little boys but loved them with everything she could anyway. But hearing these words from her mouth, it made him want to thank God, or the universe, or whoever for letting her be his mom. 

“Okay. Okay, that’s good. That’s a good response. I’d uh—I’d feel relieved to hear that if I ever came home and told you that I uh, had feelings for both girls and guys. Or—Or if Sammy did.” 

He tried to be subtle as he swiped at his eyes which meant that he nearly jumped out of his skin when his mom asked, “Okay. So, do you want to help me with the cookies?” 

“What? Oh, yeah. Yeah, I’ll help.”

He finally batted all the tears away and had pulled out the mixing bowls from the top shelf when he heard her say his name. 

“Dean?” 

“Hmm?” 

“If a hypothetical brother of a hypothetical son of mine had hypothetically mentioned that said son might have feelings for his best friend, would this hypothetical son be upset?” 

Tension pulled at his shoulders and he stopped dead in his tracks. He felt like a scared little boy again as he looked at her and asked, “Do you care?” 

Maybe it was the way he said it but her face fell into a deep frown making her rush over to him and rub her hands up and down his arms comfortingly. 

“Oh honey, of course not. We love Cas. I’d thought there might be something special between you too.” 

“That was before… before anything happened.” 

“Well moms know these things,” She said with a smile, cupping the side of his face with a cool, gentle touch. 

“Are you sure?” He asked, feeling earlier emotion try and fight its way back out. “Are you sure you’re okay with it?” 

“Come here.” She insisted, pulling him into a much-needed embrace and Dean hugged her back greedily, letting the tears fall as she whispered against his hair, “You never need to worry that there would be anything that could make me love you less. You are my baby and nothing, not a single thing in this world will make that untrue. I’ve only ever wanted you to be happy, no matter what that looks like.” 

He needed to hear those words so badly. God, he was so lucky. 

“I love you.” 

“I love you too, honey. Now, let’s make these cookies.”

**Notes for the Chapter:**

> I wish everyone could have mama bears like this. <3


	15. Decemeber 15, 2017

**Notes for the Chapter:**

> This chapter might not be the most polished but I have about 3 bangs I'm trying to get written as well so my editing time is a little limited right now. I still hope you like this one. 
> 
> Also, I didn't realize how much I love Dad!Gabriel but I love him a lot.

He didn’t realize how much he missed being back home until he stepped inside and was bombarded with all the sensory memory of his childhood. He and Gabriel had moved around a few times as Gabriel grew more and more successful in the film industry, but even stepping into the house that Castiel had lived in throughout high school, there were some things that were how he’d always remembered. 

Their formal living room was his least favorite place in the house, mostly for show when the fancy Hollywood people came over to talk to his dad, but further into their house, tucked behind a door was their loungeroom. In there his dad kept the first couch they had in their very first apartment, and the coffee table that Castiel picked out at a Goodwill. The movie posters and framed pictures on the wall were either gifts from Cas or pictures of Castiel growing up throughout the years, some with Gabriel right beside him. 

His dad tried to pretend he wasn’t a very sentimental person but underneath the large mounted TV, were old crafts Castiel had made in school and some framed artworks of the two of them Castiel had drawn when he was in kindergarten. 

His favorite ratty blanket was still over the couch and the rug that had seen more than its fair share of spills was still in the center of the room. 

He’d already flopped down on the couch and was rambling away to his dad, filling him in on everything that Castiel could think of that had been happening since the last time he’d been home. 

“–and I had this partner named Kevin who I was at first dreading partnering up with because he’s the type of student who seems way too serious about school but actually, we ended up working really well together and he was able to edit my paper with actual edits. Not like that guy Bart who told me to put the punctuation outside of the quotation marks. Actually, I think I should try and become friends with Kevin, I think that he’d make a good person to study with if anything. Maybe me, him, and Hannah could form a group. Oh! I should text that to her.” 

“Damn kid, I forgot how much you talk.” 

His dad had settled onto the oversized black leather recliner they’d bought when they moved into that house, since Gabriel thought a movie room should have a good recliner. He was looking at Castiel with an amused grin and Castiel smiled back. 

“You’re the only one who says that.” 

“Hmm, I wonder why,” Gabriel joked. “Maybe it’s because you’ve been talking my ear off since the second you could speak. I really regret listening to all those people who said I should read to you every night.” 

“Shut up,” Castiel yelled jokingly. He knew Gabriel was only teasing him, something his dad often did. 

His dad smiled. “But really, it’s been too quiet here.” 

Cas could see a hint of sadness in his dad’s eyes but knew Gabriel was trying to hide it. It probably was a lot quieter now that Cas was gone and he felt a little guilty for not realizing it until then. 

He’d probably never forget the time in second grade when the other kids made fun of him and told him he was a baby who couldn’t talk, just because he was shy. His teacher had found him crying behind a tree on the playground and had comforted him until Gabriel could get there. Both Gabriel and Ms. Mosely had told him how smart he was and how he knew more words than any of the second graders in the whole school and that it was okay that he didn’t want to talk to the other kids yet. 

From there on Gabriel made sure to always remind Castiel that if he didn’t want to talk to other people, that he’d always be there for Cas. He’d say, _‘I’m always gonna want to listen to you, so I can be the person you talk to if you don’t feel like talking to anybody else.’_ and his dad was by far the easiest person to talk to. But more than that, Cas was pretty sure he was the only person Gabriel felt like he could talk to in return. His dad often said the people in Hollywood were only looking out for themselves, so Cas really did feel bad for being so far away and leaving his dad pretty lonely. 

“I know, but I’m here now,” Cas said cheerfully. He settled deeper into the couch and kicked his feet up onto the coffee table. “What do you have planned for us?” 

“Christmas Carol tickets for Saturday, Miracle on 34th Street tickets for next Friday, and The Nutcracker on Christmas Eve-eve.” 

“And you’re making breakfast Christmas morning?” He asked, already envisioning the crepes and breakfast casserole Gabriel made them every year. 

“Absolutely.” 

“Good.” 

He fished through a couple of channels before they settled on watching holiday Lifetime movies (they may or may not have been a guilty pleasure in their house growing up). Gabe left him alone for a bit while he made some popcorn and grabbed them a few boxes of candy he always left in the pantry. 

By the time they were two movies in, Castiel realized just how much he’d been aching for home. He loved being away at college, especially spending time with Dean, but it felt so good to be home. 

“I’m so glad to be back on this smelly couch,” Cas said as he snuggled deeper into the lumpy cushions, wrapping his blanket more around himself. 

“That couch has been there for you for all your life, show her some respect.” 

He patted the armrest a few times. “She knows I love her.” 

Cas looked at his dad who was giving him a strange look before saying, “Something’s different with you. You’re—you’re being goofier than usual. It’s like you’re… happy or something disgusting.” 

Frankly, Cas was surprised he hadn’t already gone and blabbed all about his past few months with Dean. He hadn’t wanted to say anything earlier to his dad because having that as a phone conversation seemed weird, but now that he was back with him, he wanted to talk about it. 

“Actually, I uh—I have something to tell you.” 

“Oh yeah?” 

Cas sat up and pulled the blanket around his lap. He was a little nervous to even be saying this at all but if there was anyone he could openly talk to about all of it, it was Gabriel. 

“Yeah. It’s about Dean.” 

Castiel could see the ideas swirling around in his dad’s mind. 

“Okay?” Gabriel said curiously. Castiel grew a little nervous but he actually wanted to talk about this.

“We’ve uh—we’ve been hooking up.” 

He didn’t know what to anticipate when finally telling this to his _dad_ so he wasn’t all that surprised to see Gabriel looking a lot confused. 

“What do you mean?” 

“We’ve been… we’ve been having sex.” 

Gabriel’s eyebrows raised. “Oh.” 

Castiel wasn’t sure what his dad was going to say next and before he could even give him a chance to say anything at all Cas was already rambling on. 

“And I really like it. I mean I didn’t think I _wouldn’t_ like it but I didn’t really think I’d like doing it as much as I do but I think that’s it’s because it’s with Dean. I really like him. I might even be in love with him and I’m just—I’m glad I asked him to do this with me. I didn’t think anyone would ever want to do it with me since I’ve always been the weird kid, you know? I know I had friends, but guys always just thought I was invisible. But even though I thought Dean was straight he was still willing to do this with me. And I think he’s maybe starting to like me too? He keeps texting me and calling me baby. I mean we haven’t talked about it at all but I think maybe he does.” 

It all came out in a rush that he was fairly certain his dad didn’t pick up on most of it, but he did seem to want Cas to clarify one thing. 

“Just maybe?” 

Cas shrugged. He’d only recently been thinking that maybe it was a possibility but he was obviously not sure about it at all. 

“He hasn’t said,” he explained. 

Gabriel’s face still wasn’t giving much away to tell Castiel what he was thinking, and Cas was kind of grateful for it. He wasn’t sure if he could’ve handled his dad looking disappointed in him or worse… his dad being excited and obnoxious about Cas finally getting laid. 

“Is he shy about these things?” Gabriel asked. 

“He never really talked about his romantic life so maybe?” 

“You think you’re his first boyfriend?” 

To say Cas’s heart skipped a couple of beats would be an understatement. Hearing himself referred to as Dean’s boyfriend was more than he thought he could handle and he quickly corrected it. 

“We aren’t boyfriends.” 

“But you two live together, have sex together, and he calls you baby? Are you both sleeping with other people or just each other?” 

“Just each other,” Cas answered, hating that he was trembling a little at the implication in his dad’s words. 

“Kinda sounds like you two are a thing, kiddo.” 

“Really?” He didn’t care to mask the hopefulness in his voice. 

“Yeah. If it quacks like a duck…” Gabriel joked. “Are you going to ask him then, if you two are together or not?” 

A bit of anxiety built up in him at the question and he instantly blurted, “No.” 

“Why not?” 

“What if he says no?”

“What if he says yes?” Gabriel challenged. 

His small seedling of hope that Dean felt something more for him was still mostly clouded by a heaping amount of doubt. It was the uncertainty of it all that made him scared to even consider bringing it up to Dean. 

“But there’s no way for me to know for sure,” he explained. 

His dad nodded in agreement. “No, but that’s how some of the best things happen. Taking risks and trying something that scares us is the way we have to grow.” 

“Yeah but I don’t want to lose him.” 

“If you do lose him, then he wasn’t right for you to begin with.” 

He knew his dad was right but the thought of not having Dean in his life at all sounded a lot worse than just living with things the way they were. 

“But I like how things are right now.” 

“Do you?” 

“Yeah?” He said unsure. He wished he could just lie but he knew when it came down to it, he wasn’t completely happy with things how they were. If he had the chance to really be with Dean, he’d probably be a whole lot happier. 

He was fairly certain his dad knew him well enough to know what he was thinking, and he was pretty grateful when Gabriel put on his serious dad-face. 

“I know I like to crack jokes and act like I don’t take much seriously, but Cassie, I need to be a dad for a second.” 

Castiel sit up a little straighter as Gabriel turned more towards him in the recliner and gave him an understanding smile. 

“I love seeing you happy like this but I’m still going to worry about you because that’s just what I do. I love you more than I can even comprehend, so I worry.” 

Castiel nodded his understanding before Gabriel continued. 

“I don’t want you to be stuck with just being comfortable with how something is going, especially if you’re not completely happy. I don’t want you to end up like me who stays with the same person because it’s familiar and safe. If you love him, you should see if he loves you too. I just don’t want to see you settle for being ‘happy enough’ when you should have so much more than that, kiddo.” 

He felt a few tears poke at the corners of his eyes as he tried to let himself accept his dad’s words. It just seemed so much easier to accept what he had at the moment and not try to push Dean’s limits. The fear of potentially messing it all up for himself made it hard to believe that he shouldn’t just settle for being happy enough with it all. 

“I don’t know what I’ll do if he doesn’t love me back,” he admitted, hating the fact that he knew he’d probably crumble if Dean rejected him. He’d stupidly gotten too invested but how could he have not? He set himself up for failure the moment he asked Dean to agree to this arrangement. 

It seemed his dad could sense him getting upset and reached out to squeeze his hand. 

“Let’s not worry about it now, okay?” He asked. “You have a month until you see him again. Maybe this time apart will make you see things differently.” 

“Okay,” Cas agreed, despite the pit settling in his stomach. 

“How about some hot chocolate?” 

“Can we watch the Grinch too?” 

“Done and done.”

* * *

Being back home was better than Castiel had imagined. He still missed Dean but getting to text the other man all day and spend nights sharing sexts… it didn’t feel as lonely as he thought it would. In fact, he’d been spending more time with his dad than he could remember doing in a very long time. 

Most of the film and television world were on hiatus so his dad was home all day, and since he and Kali had apparently, officially, called it quits, there was no one to share his time with. 

They mostly vegged on the couch in between bouts of going to the movies and out for some meals when Gabriel was too lazy to cook and they talked about anything under the sun, much like they had when Castiel was growing up. With his dad, Cas knew there were no limits. He had never had to worry about being judged for anything he thought, said, did, or was interested in because Gabriel had practically lived and done it all. He was more relaxed than many parents were, but even Gabriel had made sure Castiel had also grown up with boundaries and morals. 

It was rare to get a dad-talk like the one he’d given him about Dean, but sometimes his carefree hat would come off and the facade he put on with most everyone in LA would be stowed away. 

Growing up Castiel had been asked more times than he could count if Gabriel really took good care of him, or if he was happy living with him. Sometimes they’d go as far to bring Gabriel to his school and interrogate him on the way he was raising Cas. And as a little kid he just didn’t understand. His dad was the best dad he could be. He helped Cas whenever he needed to, he read stories with him, he taught him how to tie his shoes and ride a bike. As a little boy, Cas just thought Gabriel was silly and he didn’t know why not everyone thought that too. 

He was proud to have Gabriel as his dad, even if he knew he wasn’t biologically his. Having someone who had his back and who he could talk to about anything that came to mind, it was special and something he’d only ever known in three people: his dad, Hannah, and Dean. 

They were snacking over their kitchen island on some French toast sticks Gabriel had made when a random thought crossed his mind. 

“Would my mom have been okay with me being gay?” 

He talked about his mom far less than he had when he was little and so curious, which was a shame because it seemed to always make Gabriel smile with happy memories of his sister. 

“Honestly? Probably not at first but with how much she loved you, I think she would’ve come around.” 

“Why not at first?” 

His dad leaned over the kitchen island and rested his elbows on the granite, pondering his words. He always seemed to carefully choose what he would say when explaining his family to Castiel. 

“Our parents were extremely close minded, especially our mother.” He started, and Castiel nodded, having heard that statement a few times before. “They both tried to instill certain beliefs in us but our mother was especially vile when it came to her opinions on different sexualities and even races. Anna for the most part didn’t agree with what our parents said but she didn’t rebel as much as I did and only knew what their limited world allowed her to know.” 

Castiel nodded again, remembering how Gabriel had once told him it took his mom until she was about twenty-four before she’d had enough with their parents and moved out on her own. He knew that she had still been pretty conservative for the most part but distanced herself from her parents’ beliefs. He also knew the most rebellious thing she ever did was get pregnant with him, by a man she never named. His mother was definitely a mystery to him but he still liked to know what she’d think of him. 

“I really think if she would’ve learned you were gay,” Gabriel continued, “if she didn’t already support gay rights before, she would’ve done _anything_ to learn about it and support you. She’d also have done anything to keep our parents’ beliefs far away from you.” 

“So, my grandparents would’ve hated me?” Castiel asked with a laugh. 

“They hated everyone,” Gabriel said sarcastically. 

“Do you miss them?” 

“Sometimes?” Gabriel pushed back from the island and moved to the fridge to pour himself another glass of the fruit punch he’d been drinking. “I think mostly I just miss having a big family. I hate that you never got to grow up with a bunch of other kids and have big family holidays. I feel like it was kinda my fault you were always lonely.” 

Cas rolled his eyes and threw a piece of his French toast at the other man, annoyed with hearing this guilty confession from him again. 

“I wasn’t always lonely. I had you.” 

Instead of saying anything, Gabriel just stuck out his tongue and then proceeded to try and catch the second piece of French toast Castiel threw at him. 

The two of them ended up in a fit of laughter once Gabriel banged his head into the cabinet trying to catch the food, but it ended up with him tugging Castiel into a hug. 

“Your mom would’ve been so proud of you,” he said with a kiss to the top of Cas’s head. “I know I am.”

* * *

Christmas crept up on him and before he knew it, he was being jolted awake by his dad in a Christmas onesie jumping on his bed screaming that Santa had been there. 

He was bleary-eyed and a little grumpy at the sudden wakeup call but crawled out of bed with his blanket still around him, making sure to grab his phone and bring it with him downstairs. 

As he waited in their loungeroom for his traditional peppermint hot chocolate, Cas unlocked his phone and checked his messages, unable to contain his smile when he saw Dean’s name right away. 

**Dean:** MERRY CHRISTMAS

_Cas:_ Merry Christmas!

**Dean:** Did you just wake up?

_Cas:_ Did you forget about the time difference again? 

**Dean:** Oh yeah

Castiel laughed despite himself. Dean continuously kept forgetting there were two hours between them. It made it a little tough to come up with excuses to his dad on why Cas was heading to bed earlier than seemed necessary during winter break when Dean wanted to get a little scandalous during their late-night texting. 

_Cas:_ Have you opened your gift yet?

**Dean:** Not yet. I wanted to wait until you opened yours. 

**Dean:** but you took foreverrrrr to wake up 

_Cas:_ I’m sorry to cause your suffering. 

_Cas:_ Want to open them now? 

**Dean:** hell ya! 

Cas waited with high anticipation for Dean to reply back. He wished more than anything that he could be there to see Dean’s face. Dean was always so excitable when it came to presents. He’s fairly sure if Dean was pranked with a piece of fruit wrapped into a present, Dean would still be giddy as hell to receive it. He didn’t doubt Dean would like his gift but he hoped Dean would really love it. 

**Dean:** Cas… 

It was clear Dean was worried about how much Cas spent on him. If the situations were reversed, he’d probably feel bad about Dean spending a lot on him but it was Christmas and Dean deserved nice things. 

_Cas:_ I know, I know it’s too much but I thought it’d look good on you.

**Dean:** I’m mad at you but I love it. 

**Dean:** I’m sorry mine isn’t as good. 

Opening the awfully wrapped present, engulfed in too much tape, Cas couldn’t stop smiling. It was stupid that he kept picturing a future of them together where Dean and Cas wrapped presents for each other, secretly, in separate parts of their home. Maybe there’d be kids… ones who would help them pick out the perfect gift for the other. It was all just a fantasy but Cas could picture it so easily despite knowing its improbability. 

He focused on opening the gift to distract from his thoughts and nearly cooed when he saw what was inside. 

At the top of the box was the most adorable crochet bumblebee, maybe only three inches long, and underneath him were five books from the bestselling list—the list he kept hinting to Dean that he wished he could find time to read them. 

_Cas:_ Dean this is exactly what I wanted. Thank you!! 

**Dean:** It’s nothing special. 

_Cas:_ To me it is. 

**Dean:** I can get you more when we get back. 

_Cas:_ Stop it 

_Cas:_ This is perfect 

_Cas:_ The bee is the cutest thing I’ve ever seen. 

_Cas:_ I love him. 

**Dean:** I thought you would. 

_Cas:_ I’ll name him Buzz. 

**Dean:** stop being so cute 

Cas’s heart did a little flip flop in his chest. It felt so much like Dean was flirting with him he didn’t know if his heart could take it. 

Not knowing what else to say, Cas took a selfie on him with the bee and sent it to his friend. 

“What’s got you so smiley?” 

Cas’s cheeks and ears were definitely red as Gabriel handed him his mug, nearly overflowing with whipped cream. 

“Just Dean. We opened our presents.” 

“Aaaand? What’d loverboy get you?” 

Cas had to roll his eyes at how obnoxiously giddy his dad was that morning but he also couldn’t help but lean into the enthusiasm a little bit. He tried to keep his cool though as he sipped from his hot chocolate and told his dad, “Just some books and this bee.” 

“Seems to know you pretty well,” Gabriel observed, adding a little eyebrow wiggle for dramatic effect. 

Still blushing, Cas tried to hide behind his hot chocolate. 

“Come on, it’s my turn to open presents,” his dad announced. 

One more quick glance to his phone showed another text from Dean. 

**Dean:** I mean it. You’re too cute. 

He just about melted and despite not wanting to get his hopes up… he couldn’t help but think that Dean’s message didn’t sound like something a friend would say. He was almost, mostly, pretty sure Dean liked him too and that was the most Castiel could have wished for that Christmas.

* * *

New Year’s Eve saw Castiel following Gabriel around some big-time director’s house, sneaking as much food as the two of them could manage and secretly whispering some jokes about the snooty people they had to speak to. Not everyone was bad though, of course, but he and Gabriel always liked to make fun of the people who tended to try too hard to appear rich. 

His favorite part of the night was the Happy New Years text he got from Dean that featured a few fireworks, a champagne bottle, and a kissy-face emoji. 

He was missing Dean so badly at that point it was a little insane. 

January 2, 2018 

_Dean:_ When do you get back in? Just trying to remember what you told me. 

**Cas:** On the 8th, my dad has a job in Vancouver that starts then and I don’t want to be stuck at our house alone. 

_Dean:_ I was thinking I might come in then too

The prospect of Dean coming home early made Cas unreasonably happy but he didn’t want to get his hopes up. 

**Cas:** We don’t start classes again for another week. Surely you want to stay with your family as long as you can. 

_Dean:_ I was thinking it might be nice to just have some time to myself without my family around and stuff. Like a little break for me too maybe

**Cas:** I’d be less lonely in the dorms if you can back. 

_Dean:_ You miss me? 

**Cas:** I wouldn’t go as far as to say I miss you but there is a certain charm to your company

_Dean:_ Yeah yeah I miss your ugly mug too 

Cas virtually flipped Dean off but he was much too pleased with the idea that he’d get to see Dean a week earlier than he’d previously thought.

* * *

Leaving Gabriel was harder than ever, despite knowing it would only be a few short months before graduation and moving back home. Still, he hugged his dad just a little tighter than usual and promised to call him all the time. 

Being back at the dorms still felt like home but he realized that he wouldn’t be able to call it that for much longer and that too made him a little sad. He was, however, shaking with anticipation. Dean had said he was about thirty minutes away about forty-five minutes ago. 

Cas didn’t know how to keep his cool. He wanted so badly to run down to the parking lot and just throw himself at Dean the minute the other boy was there but he didn’t want to seem too desperate to see him. 

He was also nervous about what he was supposed to do when Dean got back to their dorm room. Was Cas just supposed to wave and welcome him? Was he supposed to hug his friend? Would it be okay to just run to him and throw his arms around him like he’d been fantasizing about? 

He didn’t want to do something that Dean would think was stupid. He wanted to just follow Dean’s lead but he was scared Dean wouldn’t be very excited to see him. They had talked over break, and flirted a little when they’d talk late at night, but did it even mean anything? He just didn’t know. He was always so confused where they stood. He wished Dean could outright tell him if there were any feelings there. 

Cas would understand if Dean might have feelings but wanted to keep a relationship a secret from other people. Coming out was hard and it might take Dean time to get used to if that was what was happening. But he didn’t know. Did Dean even like guys? Maybe he was ashamed for enjoying what he and Cas were doing and that was why he didn’t want to ask for anything more. Maybe him enjoying it was just a fluke and when they were done he would go back to only enjoying sex with girls. 

Cas wanted so badly to give them a shot but he wanted Dean to say _something_ that would make it clear Cas wasn’t just taking a shot in the dark. 

When the door clicked open, he thought his heart was going to fall out of his stomach. 

He stood up, thinking it’d be rude to just stay seated on the couch as Dean lugged his duffle bag inside but Cas still found himself routed to his spot, staring at Dean who just walked in. 

“Heya, Cas.” 

“Hi.” Cas said awkwardly with a wave. 

“You wanna help me? I have another bag down in the car with my presents and shit from my parents.” 

“Oh right, of course,” Cas fumbled, rushing over to grab Dean’s duffle from him so the other man could rush back down to the parking lot. 

He lugged Dean’s duffle over to his bed and dropped in on top of the comforter before standing awkwardly in the room as he waited for Dean to come back with his second bag. 

Dean smiled at him a little when he finally walked in and dropped the bag by the door and Cas was still standing there feeling completely unsure of what to do. Figuring he probably was in Dean’s way he moved to walk back around to the futon but Dean grabbed his arm. 

“Hey, come here,” the taller man said, pulling Cas in towards him. That’s when Cas realized Dean was pulling him into a hug and quickly latched onto his friend. He was almost suffocated a little with how tightly Dean’s arms wrapped around him and it felt a whole lot like Dean missed this as much as Cas had. 

“Missed you,” Dean whispered against the collar of Cas’s shirt. 

“I missed you as well.” Cas got to hold onto Dean longer than he expected he would, and maybe Dean realized the same thing too because he pulled back and patted Cas on the shoulder. 

“How was your break?” He asked, sounding about as awkward as Cas felt. 

“Good. But you know that. How was yours?” 

“Good, but you know that too.” 

They looked at each other with equally clueless expressions before bursting out laughing at their ridiculousness. 

“Do you want to watch a movie?” Cas finally asked, which earned him a bright smile from his best friend. 

“Duh.” 

They settled in nicely into the futon, side by side like they always were but Castiel felt nervous energy radiating off of him. It was like his body insisted Dean was a stranger again, or he was just too caught up in fantasies that his mind couldn’t understand nothing was actually going to happen between them outside of their usual arrangement. And to be honest, it looked like Dean wouldn’t want to do anything sexual with the way he continued to heavily blink and rub his eyes. 

“Are you alright?” Cas asked after a while, watching Dean fight off sleep for the better half of their movie. 

“Hmm? Yeah,” Dean said with a husky voice. “Just really fucking tired. That last leg of the drive really took it out of me.” 

“Do you want to go to bed?”

“No. I like hanging out with you,” he replied, nudging Cas with his elbow. 

“I could lay down with you?” Cas suggested. “I could watch the TV from your bed that way?”

He wasn’t sure if Dean could see straight through Cas’s desire to sleep in his arms again, but his friend smiled and nodded his head in agreement. 

“Yeah. Yeah, okay.” 

They got ready for bed pretty quickly, doing the absolute bare minimum needed to have clean teeth and pajamas on. 

Castiel knew how much he’d been missing having Dean by his side at night but getting to feel it once more shocked him at how completely natural it felt to snuggle down against the mattress and let Dean’s head rest on his shoulder. The way Dean’s arm curved around Cas’s waist and pulled him close, fit like nothing else. 

“You’re comfy,” Dean whispered, making Cas’s cheeks pull into a smile. 

“Good. Get some sleep.” 

Dean wasn’t kidding about being exhausted because it took him no time to start softly snoring against Cas’s chest. The movie that was across the room from him on the TV became secondary as he found himself in awe at the level of trust and comfort Dean had to feel being able to sleep against Cas’s chest like that. It felt special to get to hold his friend and Castiel could easily see himself doing it for the foreseeable future. If he was lucky he’d get to have it for much, much longer. 

The thought was enough to help him drift off to sleep as well.

* * *

Cas woke up to the feeling of Dean sleeping across his chest still, and a very, very numb arm. Dean looked so peaceful that Cas almost felt the urge to continue on with his discomfort but the pins and needles were a little unbearable. As gently as he could he shuffled his arm out from under Dean’s neck and turned onto his side, softly grabbing Dean’s arm and moving it back around his waist as he moved his back to Dean’s chest

He managed to drift off to sleep for a few more minutes before he woke again to the feeling of Dean nosing into the hairs at the back of his neck. A full body shiver wracked through him at the sensation. 

“Morning, baby,” Dean yawned against his skin and Cas practically melted at the pet name, having not heard it in person for over a month. With a smile, Castiel rolled over onto his back and 

“Did I drool on you?” Dean asked, wiping away the evidence from a great night’s sleep. 

“I didn’t mind.” Cas teased back, trying his best to wink. 

“I’m still a little sleepy.” 

“That’s okay, we don’t have to get out of bed yet.” 

“Good.” 

Dean’s hand trailed lightly over his belly, tickling a little from the gentle touches. 

He forgot how good it felt to have Dean’s hands on him, to feel the softness of his fingertips and slight roughness to his palms as the moved over his skin. He could feel his breathing getting a little heavier as Dean continued his touches. 

He could tell Dean’s intentions shifted when the man was no longer idly tracing patterns over Cas’s belly. Dean’s palm found its way up towards Cas’s chest, and suddenly he was tugging a little at Cas’s nipples and thumbing over them to sooth them right after. The sensation had Castiel rapidly hardening in his pajamas, and trying his hardest to bite back a moan but Dean didn’t let that slide. 

“Let me hear you,” he whispered hotly against Cas’s ear. All Castiel could do was nod. 

It was as if Dean wanted to find the fastest way to pull noises out of him because within moments Dean’s hand had slid down his chest, down his stomach, and under the waistband of his pajamas, wrapping around his cock without hesitation. 

“Dean,” he groaned looking over at his friend with a shocked expression but Dean’s eyes held no regret, just deep dark need as he started to slowly stroke Cas’s member, not breaking eye contact for a moment. 

Both their breathing grew heavy between them as Dean continued to pull at tug at Cas’s length, earning him moans and whimpers that Castiel refused to keep quiet at that point. The fact that Dean was choosing to touch him like this made his mind a little muddy. 

When Dean asked for a little bit of lube and for Cas’s pants to slip off, Castiel thought he was going to lose his mind. Dean’s hand was sure and fast, rapidly bringing him towards the edge and there was nothing Castiel wanted to have more than this. Right as he was about to come, he found himself burying his face against Dean’s cheek, squashing his nose against it, and gripping at the edge of Dean’s hair. He was certain the sound he made sounded like he was dying as he finally came, his whole body tensing up as his come splattered against his stomach and chest. 

He felt like he’d been running a marathon by the time he’d released his vice grip on Dean’s hair and had settled back onto the pillow. He was panting a little, still as he looked to Dean who was watching him intently. 

Staring at each other was more intimate than Castiel knew how to handle. He didn’t want to convince himself that the way Dean was looking at him meant anything, but it _felt_ like it did. It felt like Dean wanted to kiss him as badly as Cas wanted to be kissed by Dean but neither one of them were making the move to do so. 

He was too scared to try, even when Dean was looking at him like that, but the uncertainty inside of him continued to hold him back. He felt like a coward. 

Maybe Dean grew tired of waiting or maybe he realized the moment between him and Cas was too intense, but the green-eyed man pulled away, smiling tightly at Cas. 

“I should probably get us both cleaned up.” 

It was then that Castiel realized he hadn’t done anything for his friend in return. 

“Wait, let me suck you or something.” 

That made Dean laugh. 

“I think I’m handled,” he admitted looking down towards his crotch. Cas couldn’t see anything but he was reasonably certain Dean had came in his pants. 

Once Dean had made it off the bed and had entered the bathroom, Castiel ran his hands down his face wondering how the hell he was ever going to get Dean to share how he was feeling… if he was feeling anything at all.

* * *

The beginning of their final semester crept up on them sooner than either of them would have liked and Cas wasn’t sure how he felt about it. It felt like he’d been sprinting so long throughout college and now that he was close to the finish line, he wasn’t sure he wanted to finish at all. He was tired of homework and essays but he was also scared of the future. What did graduation mean? He hadn’t even figure out what clothes he wanted to wear for the day, let alone what he wanted to do with the rest of his life. 

It was all so terrifying yet it had an undercurrent of excitement too. No one could tell what the future would bring, and it was equal parts horrifying and magical. 

But Castiel was mostly just nervous. 

He woke up a little too early for the day but he decided he’d clean up a bit, eat some breakfast, and get ready… and if he was really lucky maybe he and Dean could have some ‘Pre-last-first-day-of-class sex.’ Only, it had been a while of Cas hustling and bustling around the room and his roommate still hadn’t gotten out of bed. 

Cas knew Dean had a class an hour before he did, and that his friend needed to leave in twenty minutes so he made sure to attempt to wake his friend just in case. 

As gently as he could he nudged his friend until he saw his favorite set of green eyes blink open. 

“Dean, I don’t think your alarm went off,” he explained. “You have class in twenty.” 

“Fuck,” Dean groaned, sitting up. He looked completely wiped still, leaving Cas to wonder if he’d had a bad night’s sleep. 

“Is there anything I can do for you?” Cas asked, trying to be helpful. 

“No I’m good,” Dean answered through a yawn, sliding out of the bed with heavy movement. “I’ll just go like this.” 

“I’ll grab you something to eat.” 

Cas went to go grab something from under his bed where he stored some of his food, but Dean shook his head. 

“Not hungry, but thanks.” 

“Are you sure?” It didn’t seem like Dean to turn away some food, especially food he could snack on later when he was hungry. 

“Yup,” Dean said shortly. He grabbed his backpack and headed to the door, but Castiel’s gut said something was a little off. 

“You okay?” He asked. He worried a little that Dean may have had a nightmare that night. Dean had been sprawled across his bed fast asleep by the time Cas had gotten out of the shower so he ended up sleeping in his own bed for the night. He felt a little guilty that Dean may have had some bad dreams that messed up his sleep or something. 

“Yeah, I’m good,” Dean said with a shrug followed immediately by a jaw-popping yawn. “Just tired. I feel like I haven’t gotten my sleep back in order since break.” 

Cas didn’t feel like that was all it was but he let it slide, knowing Dean had to get to class. He figured he could try some creative ways to help Dean get some better sleep later, for now he had his last first day of class to attend.

**Notes for the Chapter:**

> I hate to remind you all of this but bumpy roads will be here shortly.


	16. February 14, 2018

**Notes for the Chapter:**

> Just a heads up, in this chapter it is implied that Dean is dealing with depression/seasonal depression.

He was so tired, all of the time lately. At first he thought he was coming down with a cold or something but when a week had passed and he still just felt groggy, he knew he wasn’t sick. He was trying to ignore it and pretend like nothing was wrong, like he did with all of his problems but he could tell Cas had already picked up on his mood shift. 

Cas, the angel that he was, kept trying to cheer Dean up, bringing him snacks or choosing to watch some of Dean’s favorite movies so Dean played along and pretended like it was working. It’s not that he didn’t love the attention or kindness, he did very much, but some stupid part of himself couldn’t get excited over it like he used to. But he kept on pretending, waiting for it to pass because as much as he wanted to just stay in bed and sleep off the funk, he had things to do. 

Those things started to get a little more difficult as he kept pushing himself through the sludge. Remembering to set his alarm, choosing to hop in the shower before bed, and getting started on his homework felt like chores but he kept on keeping it to himself. 

He felt like he was doing a pretty good job of hiding it for the most part. 

The part that sucked the most was how in an out he was. Some days weren’t as bad as others and other days he could hardly remember if he’d even made it to class. His autopilot was practically in full gear. 

He did, however, feel good on his birthday, which was all Cas’s doing. 

On the actual day, Cas had gotten him a chocolate cupcake with a sparkler candle and almost set their dorm room on fire. They’d laid together in bed that night and Dean had gotten to give Cas pleasure with his hand again, and watch Cas fall apart right next to him. He hadn’t been too revved up himself but he was pretty sure Cas didn’t know that time either. 

He was still into it, God he was still so into it, but for some reason his body wasn’t really at the time. Just another stupid fucking side effect. But Dean tried to not let Cas know. For days he tried to just focus on Cas, and when he was feeling in the mood on his better days, he made sure they went full force. 

One thing that hadn’t changed was how much Dean craved being close to Cas. He wanted to be next to him any chance he could get, and thankfully even though they weren’t having as much sex as they used to, Cas was still crawling into Dean’s bed at night and sleeping next to him. Except for the nights Dean gave into his exhaustion and passed out before Cas was even in his pajamas—those nights sucked. 

His dreams weren’t bad, yet, but they were odd, jumbled nonsense that left Dean feeling confused and a bit out of it as he woke up, searching for Cas to make sure he was close. He tried to be grateful he wasn’t having nightmares but he was honestly starting to get pretty pissed off with himself. 

He knew what this was but he hated that he was even dealing with it to begin with. He knew it would blow over eventually, probably a couple of weeks like it always did. He knew it was probably just the season and it being darker and colder out but he’d get over it. He had before. He even made sure to pick up some vitamin D from the drugstore because he could handle it on his own, thank you very much. It wasn’t a big deal, not enough to have to talk to anyone else about it. 

He was fine. 

At least he had enough sense about him to notice when pink and red heart balloons started popping up at stores and around campus. He wasn’t really sure when January had ended and was suddenly days before Valentine’s day but he knew, despite his funk, he wasn’t going to miss a chance to do something really nice for Cas. 

On principle, Dean usually hated Valentine’s Day. He tried to ensure he was single and far away from single girls at that time because one, he didn’t want to buy them a gift, and two, he didn’t want them to think he wanted something serious. 

But now? 

Now he wanted something as serious as serious could get. With Cas, Dean actually saw a future. He could picture the two of them together for years. Dean was almost positive Cas was it and he was really, honestly, trying to work up the courage to tell him. 

His plan was Valentine’s day as cliché and stupid as it seemed, but he was going to try. 

He hadn’t actually asked someone out since… well, since high school maybe. Even then he’s pretty sure they had gone from being friends to just telling people they were together. So, to say he was nervous was an absolute understatement which was why he fumbled it big time when he finally tried. 

“Since when are our friends such giant saps?” 

Cas was cleaning up his desk while Dean sat on the futon fidgeting so much with his hands he thought he might actually have to sit on them. 

Without looking up from where he was stacking notebooks Cas asked, “What do you mean?” 

“Seriously everyone is going out on a special date tonight. Even Ash and Benny scored some,” Dean was trying to sound casual and gauge where Cas’s mind was when it came to Valentine’s Day. They’d never really talked about it before, usually choosing to pretend the holiday didn’t exist and just watch movies or order too much take out, but now Dean realized he wanted to know if Cas thought the holiday was cheesy or not. 

“Hannah did as well,” Cas seemed to realize. He stopped cleaning for a moment but didn’t turn to Dean when he spoke. His voice was mostly just a big mumble as he said, “Uhm, if—if you’d like to go out and try and… meet someone. I—I’d understand. I could use some time to catch up to you on Game of Thrones finally.” 

At first, Dean’s heart dropped a little thinking Cas was telling to go out and find someone else but then Dean realized… did Cas sound a little jealous? 

“What? Meet someone? Hell no,” Dean rushed to say. “No, that’s not what I was trying to say.” 

Slowly Cas turned to look at him. 

“Oh.” 

Dean shoved his hands under the crooks of his knee to keep himself from wringing them further as he worked up the courage to finally spit out, “What about we make dinner tonight?” 

It might’ve been his imagination but it looked like Cas’s breath caught a little. 

“You want to go to the kitchen and actually cook something?” His friend asked rather skeptically. 

It wasn’t a no, and that somehow made Dean just a smidge less nervous. 

“No one will be here tonight, so no one will be there to try and mooch off our food, we could do something nice?” 

Cas stared at him for a while before nodding, “Okay. What do you want to make?” 

They had limited fridge space since they could only use their mini fridge which housed mostly iced coffee and water bottles, so he didn’t already have the groceries needed, but he hoped his plan was at least appealing to Cas. 

“I was thinking I could cook up some steaks and make like a pasta salad or something?” 

It was hard to tell what Cas was thinking, but his friend nodded again and said, “That sounds nice.” 

“Then let’s go to the store and you can pick out desert?” 

They didn’t really acknowledge it was Valentine’s Day, even when they were at the store together waiting behind people carrying large stuffed animals, bouquets, and boxes of chocolates. They didn’t do much more than nervously laugh when the lady wished them a ‘nice date night’ as they checked out and grabbed their grocery bags. 

They still didn’t say anything as they cooked together in their residency’s kitchen, side by side, talking about who knows what but smiling the whole time. 

And when they were able to take their dinner outside onto a small patio, just the two of them, it felt really freaking special and Dean knew he wanted so many more nights just like that. But the night wasn’t quite over yet. 

With dinner cleaned up, Dean felt anxious to make the rest of the night good. The dorm was mostly cleaned up, though he wished he would’ve had the forethought to try to make it a little nicer. 

They kept the lights off when they walked in since Cas’s salt rock lamp was alright on, illuminating the room in a warm glow. 

They both could tell by their lack of conversation that they both wanted the night to get intimate, but Dean didn’t want just a standard roll in his bed. He wanted to make it feel a little more special. 

“Do you want to shower?” Dean asked, knowing Cas liked having some time to get as clean as he could. 

His friend nodded then almost in a whisper asked, “Do you want to shower with me?” 

“Yeah,” Dean answered immediately. It was something he’d wanted to do for a while and he couldn’t really believe Cas was asking him. “I’ll meet you in there in two minutes.” 

“Okay.” 

Not wanting to waste any time he had to get Cas wet and naked, Dean rushed into their living space and surveyed the room. The light from the salt lamp made the place look quite sexy but there was something he still wanted to do. 

He’d had this idea before but had never actually taken the time to do it. Without making too much of a ruckus he lowered their futon down into a full bed, drastically bigger than their twin beds. He pulled the pillows of their beds and placed them as nicely as he could on the futon and kept a blanket nearby that they could grab once they were ready to sleep. He made sure the lube and Cas’s box of toys were nearby (just in case) and headed back towards the shower. 

The water was already on and Cas had continued with the theme of keeping the lights dim, only using the nightlight on they kept in the bathroom so they wouldn’t be blinded in the night. 

Their bathroom wasn’t anything to write home about, especially not their too-small shower that could hardly fit one of them, let alone two, but neither of them cared as they stripped down and stepped under the warm stream of water. 

At first neither of them seemed to know what to do now that they were so close, with water pouring down on them and they each found themselves looking around until they locked in eye contract, laughing with each other at how oddly they were behaving. 

Cas was the first one to move, reaching towards the soap and gliding it across his body as Dean watched with hungry eyes. He felt completely in awe of the fact that he got to be the one to watch that, to see the person of his dreams in such a domesticated way. He could already picture so many mornings like this, or nights after other dates they’d go on, unwinding with each other with a warm shower—maybe a bath where Dean could hold Cas against him with the glow of candles all around them. 

He was so in love with Cas he was certain it was going to consume him. 

A little dumbfounded by that realization, Dean almost didn’t realize that Cas was staring at him, holding the soap to his chest with a shy smile. 

“What?” Dean asked, acknowledging the look. 

“Can I—can I wash you?” Cas asked, unsure of himself. The thought that Cas wanted to run his hands over Dean’s body without any inherent sexual reason to, made his heart skip a few times. 

“Y-yeah. Yeah okay.” 

He tried to not focus on how intimate it was to feel Cas’s hands on him in such a seemingly innocent way. It felt like, with the way Cas’s hands were less forceful, less confident that maybe his friend was feeling that way too. Slowly Castiel dragged soapy hands over Dean’s shoulders and chest. He rubbed at the knots forming at the base of his neck, just hard enough to make Dean sag a little into the touch, dying to reach out and hold Cas against his wet body. His friend’s fingers moved over his skin, lingering over the softness of Dean’s stomach, making Dean flush in embarrassment but Cas didn’t seem to notice. 

It was when Cas’s hands traveled farther south that the touch felt more confident and Dean stopped worrying that he was going to throw Cas against the wall and kiss him senseless. Dean felt a soapy hand wrap around his still soft length. It wasn’t even sexy feeling Cas clean him but something about the moment had heat flooding downwards. He’d never showered with a partner. Never felt the desire to be slippery and half freezing and half under the water as they hogged the warmth. But now... he saw the appeal. 

Dean’s hand settled on Cas’s hip as his friend tugged a little more forcefully on Dean’s member between them and he realized how badly he needed to show Cas just how much he wanted him. 

“Turn around.” 

Castiel nodded again and turned away from Dean, the dim light from the room just barely reflecting on the curve of his back. Dean wanted to completely devour the sight in front of him but he had a plan for the night and could afford to get distracted. 

Not sure what else he could really use, he used a dollop of conditioner to slick up his fingers, pressing as much of his body against Cas’s back as said fingers found their way down Cas’s crack and towards his tight hole. 

It was like a wet dream feeling the way Cas’s back arched into the touch as Dean pressed his middle finger inside of his guy, reveling at the breathy moan Cas couldn’t help but release. The sounds Cas was making almost turned Dean to mush but he kept himself focused as he pressed one, then two fingers in and out of the other man’s hole, stretching it open. 

When he was certain Cas was about to demand Dean fuck him, Dean reached over and turned off the water, laughing at Cas’s petulant protests. 

Dean stepped out of the shower with a smile and grabbed his friend’s towel, wrapping it around Cas before grabbing his own and quickly drying off. 

They both dropped the towels on the floor as they walked into their living space, Dean’s nerves suddenly coming back with a full force as Cas took in the sight of the futon in the middle of the room. 

“I—I feel like we haven’t really done it this way before and I thought, tonight we could?” He said nervously. Cas continued looking towards the futon in the room. 

“Okay.” 

It was still difficult to tell what Cas was thinking or feeling but Dean counted it as a good sign when his friend crawled onto the bed and sat in the middle, looking at Dean with wide, trusting eyes. Dean wanted nothing more than to clamber on the bed and kiss Cas for all he was worth. He wanted to press Cas into the thin mattress and run his lips across the high points of his cheeks, down the roughness of the scruff that was still lingering on his jaw; he wanted to move his mouth lower and suck bruises against the curve of Cas’s neck and lick across the plains of his chest. 

Tonight. Tonight, he was going to try and be brave. Tonight, he was going to make it a night they wouldn’t forget. 

“I wanna try something tonight,” he heard himself saying, earning him an intrigued look from his friend. 

“Yeah?” 

Dean crawled onto the futon also and nodded, “Mhm.” 

As Dean moved closer into Cas’s space, the other man laid back with his head against the pillows, his legs opening enough for Dean to crawl between them. 

“Okay,” Cas said, his breathing already starting to come out faster. 

The things Dean wanted to say were at the tip of his tongue but actually vocalizing them terrified him. How was he supposed to say that he’d fallen in love with his best friend and wanted to spend the rest of the night proving it—the rest of his life even. How was he supposed to say those words when he’d only ever told three people in his life that he loved them and those three people were his family? 

He couldn’t say it yet but he could make love to Cas and make it the best he’d ever given the other man and maybe by the end of it the words would just fly off his tongue. 

His hands found Cas’s calves and traced small circles up them, encouraging the other man to spread his legs just a little bit wider. 

“Can we take it slow tonight?” Dean asked in a whisper. 

Something was different in the way Cas looked at him and Dean let himself believe Cas was feeling the way he was too. 

When Cas answered with, “anything you want,” Dean couldn’t hold back anymore. 

He flipped Cas over to his stomach and took in the sight of his gorgeous skin, and decided he might as well put his hands all over it since it was just too beautiful to resist. Since he had all the time in the world and it was Valentine’s day, he wanted to make Cas feel amazing. He wanted to make Cas feel how much Dean wanted to keep his hands on him, so Dean reached for some lotion and began working his fingers into his friend’s muscles. 

Instantly he was gifted with the sounds of Cas’s pleasured sighs and that sound alone made Dean want to discover each and every sound his guy could make. He let his hands roam around, rubbing and kneading every part of Cas’s skin he could reach. 

“Mmm, I’m gonna fall asleep,” Cas finally mumbled against the pillow at his cheek. 

“Can’t have that, can we?” Dean said with a smile. 

He had Cas flip back over onto his back where he decided to spend just a few more minutes rubbing lotion across every part of Cas’s skin he could reach, until he couldn’t stop himself from taking Cas’s cock in his hand and bringing it back to life. He watched Cas’s eyes fall shut and something about seeing that blissed out look made Dean fill with adoration. He kept his one hand moving over Cas’s length but reached out with his other hand to take some lube before bringing his fingers back behind Cas’s balls and finding his hole once more. 

Immediately Cas pulled his legs up to allow Dean easier access. He took his time and kept his movements slow, in no rush to get on with it, just wanting to have any reason to touch Cas as long as he was allowed. 

It was only when Cas rasped, “Dean, please, I want you inside me,” that Dean slipped his fingers out and got his own cock ready. 

He didn’t want Cas in a different position yet, especially since he was being indulgent that night. He felt closest when he could look at Cas under him like this, getting to stare straight into his eyes as he lined up his cock with Cas’s hole and slowly pushed in as Cas opened up for him. Watching every movement of Cas’s face from his lips parting, to his eyes scrunching closed just for a moment as the thickest part of Dean’s length pushed through, then watching as Cas stared up at him as they were fully connected…. It was better than anything Dean could have imagined. 

He wasn’t planning on taking things quickly, no, he wanted to take it as slow as he could for as long as he could. He wanted Cas to crumble in his arms as Dean sank into him over and over, in every position they could manage until their legs were trembling and their skin was covered in sweat. 

And that’s just what he did. He moved in and out of Cas, fast enough to feel good but slow enough that he wasn’t at risk of ending it all too soon. 

They stayed face to face for a little before Dean wanted to feel Cas on top of him. Then, the way Cas liked best, he took Cas on his side, his hands gripping at Cas’s hips as he pushed in hard but slow. 

When Cas crawled onto his hands and knees, arching his back as Dean sank into him, Dean couldn’t help but start to get carried away. Hearing the way Cas would moan his name, feeling the sweat start to pool at the base of his guy’s spin, it was so damn perfect. 

He still wanted to kiss Cas so damn bad. So god damn bad that he couldn’t resist at least getting his mouth of Cas’s skin. 

He pulled Cas up onto just his knees, plastering his back against Dean’s chest. As Dean kept thrusting, he wrapped his arms around his friend, holding him close so he could nose along Cas’s shoulder, biting and licking his way up to the curve of his neck. Right as Dean’s teeth grazed over the cord of Cas’s neck, his friend let out a full body shiver, tilting his neck further in invitation and Dean gave in to his desire to suck a mark right onto Cas’s skin. It must’ve been something Cas enjoyed since his hand suddenly gripped the base of Dean’s hair and kept him there until the mark was well and thoroughly dark. 

Just one wasn’t enough though. 

Dean couldn’t fathom not getting to trace his mouth over Cas’s skin and leave marks on every part he’d fantasized of. 

He pulled out of Cas gently and urged his friend to lay back down on the bed before laying down atop of him and finding his mouth right back on the spot on Cas’s neck. 

Cas’s arms encircled him, keeping him close as he left two more marks on the other side of his neck before starting to trail his mouth down. He licked and nipped at the skin of Cas’s peck—above his heart—before following a path down his sternum, and lower to his belly where he left a few more bruises where he could. 

It was when he had sunk low enough that his mouth landed right under Cas’s navel that Dean realized what his real goal was all along. 

He wasn’t sure if it was something Cas wanted. It was something he never asked for, but already with Dean’s mouth moving across Cas’s belly in movements that could easily be considered opened mouthed kisses, Cas wasn’t turning away Dean’s attention. Still, Dean wanted to make sure Cas knew his intention so he continued licking, nipping, and kissing his way to the junction between Cas’s hip and thigh until he could suck a deep bruise on the inner part of Cas’s thigh, merely inches away from where Cas was aching and hard. 

He made sure to make a matching mark on Cas’s opposite thigh before he was brave enough to look up. 

Cas was, unsurprisingly, looking at him with heavy-lidded eyes and unabashed hunger. The look made Dean brave enough to do what he’d been craving. With careful movements he brought his hand back to Cas’s cock and stroked it firmly, making the blue-eyed man hiss in sensation. It really was a nice looking dick, or maybe that was just because it was Cas’s; and maybe because it was Cas’s, Dean felt no hesitation as he brought his mouth to the base of it and pressed open mouth kisses against it until his mouth encircled the tip and he let the taste of his best friend fill him. 

He wasn’t completely certain if he’d imagined it but between the pounding in his ears and Cas’s heavy breathing, he was fairly certain he heard his friend breathlessly mouth, “oh my god.” 

It wasn’t even Cas’s sounds at that point that were getting to Dean, but that fact that he actually had Cas’s cock in his mouth after all this time. It was both exactly like he expected and nothing like how he imagined it would be. Cas tasted salty but felt much smoother against his tongue than he had imaged him to. He knew he was probably terrible at doing it, but he tried to do what he was sure Cas had done for him, sucking and bobbing at the head while he kept his hand moving along the shaft. 

He probably could’ve kept it up for much longer than he had but Cas tugged at his hair and rasped, “Dean, stop—stop I’m gonna come. Not yet.” 

Dean pulled off slowly, leaving a gentle kiss at the tip of Cas’s cock before pulling himself up to his knees. 

It all felt so different. Their sex had always been incredible but something about the night definitely felt overwhelming as Dean stared at his best friend. They were not quite done yet, though he knew they were both probably not going to last much longer. 

“How do you want—” Dean started to ask but Cas cut him off. 

“Like this again.” 

Moving closer, Dean hooked Cas’s legs over the crooks of his elbows and bent his man nearly in half as he lined his cock back up to Cas’s entrance. Before he pushed in, he noticed the way Cas was trembling, staring up at Dean with wide eyes. 

“You’re shaking,” Dean whispered, certain Cas knew he was asking him if he was okay. 

“I just—It feels new. I don’t know why,” Cas explained. It was a relief that Cas was feeling the way Dean was, maybe a bit nervous too since it seemed like Cas didn’t know where to put his hands or he too couldn’t get enough of touching Dean. But once Dean lined up again and began pushing in, Cas let his fingers lock in the hair at the nape of Dean’s neck. 

There was nowhere for them to look but at each other. 

“I’m gonna take care of you,” Dean promised, slowly building up his speed. 

“You always do.” 

He was overwhelmed with emotion at how tender Cas’s voice sounded and let himself be pulled down by Cas’s arms until he could bury his nose in Cas’s neck. 

He was already so close but he still didn’t want it to end. He wanted to stay like this, as close to Cas as he could possibly get for as long as he was allowed. 

All along, this was how it was supposed to feel. This is what people meant when they said that sex was special, sacred even. The desire to show someone just how much they meant to you, to want their pleasure to come before your own, to feel completely as one being and know they were the only person you wanted to be close to in that way ever again. He wanted to build a home within Cas. 

He never knew it was possible to love someone this much. 

The thought terrified him, just a little, since he was still unsure how Cas felt in return. But maybe with the way his friend held him close it meant something good? 

“Oh, Dean—” 

“I’ve got you, Cas,” he promised into his friend’s ear. “I’ve got you.” 

“Please, please, please. Touch me.” 

They’d been at it for a while, who knows how long, and Dean wasn’t about to deny Cas’s request. He pulled back just enough to get his hand in between them and start stroking Cas in time to his thrusts. 

The blue-eyed angel seemed completely lost to the moment with his eyes closed and his hands gripping at the fabric of the mattress. Dean was completely breathless by the sight of it. 

He released Cas’s legs from where they were on his arms and reached with his free hand to grip one of Cas’s above his head, bringing them so close Dean could feel Cas’s breath against his lips. 

“You’re so fucking beautiful,” Dean confessed, the words tumbling from him without permission but the way Cas opened his eyes and looked at him made the slip worth it. 

They were on the edge, just a little bit more and Dean would be tumbling over. He picked up the speed of his hips and reluctantly let Cas start to stroke himself the way he needed. 

Nose to nose, Dean wanted so badly for Cas to close the last inch of space between them. He wanted Cas to be the one to seal it between them and show Dean that he wasn’t the only one completely in over his head. Dean wanted to be the brave one but with the chance just centimeters away he willed Cas to know how he felt and to be the one to take the final leap. 

But it didn’t happen. 

They were too close and there was no turning back. 

Dean’s orgasm was rushing to him at rapid speed, and he need he needed to pull away soon. 

“Cas, Cas, Cas, Cas, Cas…” He murmured, over and over as he felt his balls start to draw up tight. 

Right as he found the strength to start to move away, Cas’s hand that was still in his gripped him tight.

“Don’t pull out,” He commanded. “Please.” 

And that’s all it took for Dean to finally fall apart. 

It rushed through him in waves, making his entire body tighten and his toes curl up until they were cramping. He could feel Cas orgasming underneath him and around him and when Dean couldn’t hold his own body up anymore, he collapsed into Cas and let himself be wrapped up in his man’s strong, sweaty arms. 

They stayed that way, hugging each other for a while, breathing in sync as their muscles unclenched and they could slowly pull apart. 

As little as he wanted to, Dean knew he was crushing Cas and had to roll off of him. He flopped onto his back, his left arm still tucked behind Cas’s shoulders, as they both stared up at the ceiling. 

Cas was the one who offered to get up and clean them up which Dean was grateful for because he didn’t think he’d be able to move his legs for days. 

It wasn’t long before they were clean and warm under the blanket with Cas’s head resting on Dean’s shoulder. Cas’s arm was thrown across Dean’s waist and Dean couldn’t resist trailing his fingers up and down Cas’s skin. 

It felt too perfect to be real but Dean knew it all had to do with Cas. Cas was a dream. It was so fucking perfect in every way, Dean didn’t know what to do with himself. His friend was kind and so fucking smart. He knew how to make Dean laugh and feel better on shitty days. He treated people with love and care no matter who they were. Cas made the world a really amazing place to live and Dean loved him. He loved him so damn much. 

He should’ve said something then. It was right there, about to cross his lips, but Cas started speaking first. 

“I—I don’t know how to say this,” Cas whispered, keeping his head on Dean’s shoulder. He sounded nervous and Dean’s heart picked up a little, worried yet excited for what that could mean. 

“Say what?” 

“It’s—This, this has been so good. All of this with you.” 

Dean’s heart warmed by the words. “For me too,” he whispered back, feeling a little breathless. 

“Just—thank you for helping me and for doing this when it probably made you uncomfortable at first. It means a lot that you’d still do this for me.” 

“It didn’t make me uncomfortable. I wanted to help you,” Dean responded honestly. He was so damn grateful that things worked out how they did and that he got to have _this_ because it was probably in the top best things that had ever happened to him. 

He wasn’t sure how to feel when Cas said, “You’re a good friend.” 

“Thanks, Cas.” 

Cas sat up just enough to look down at Dean. He was smiling softly but seemed too nervous to look Dean in the eye. Instead he focused on tracing patters on Dean’s chest as Dean tried to keep his heart from tumbling out of him. 

“That’s—that’s not all I wanted to say,” Cas explained and all Dean could think at that moment was _’please let this be it.’_

“It’s just… we’ve been doing this for a while now and—and I just… Things have… things have changed for me, a lot. A-and I get that they maybe haven’t changed for you and that’s okay. They don’t need to change. It can all stay just the way it is but… I just… I just want you to know that if that’s how you want it… it’s enough for me. I won’t ask for anything more than this. I’m—I’m happy with just this too.” 

It wasn’t what Dean had expected to hear. Not even close. He didn’t really know what to say either. Did Cas really still doubt how Dean felt? Was he really happy with things just going on the way they were? The two of them circling around something great but not taking the leap? By the way his eyes strained a little as he smiled, Dean was pretty certain Cas wasn’t being fully honest. 

He should’ve just confessed it all there. Set Cas straight about how he felt and let him know that this wasn’t good enough, not by a long shot, but something stopped him from being able to. His gut twisted and he tried to keep the sadness off his face as Cas stared at him with clear nervousness. 

“Okay,” is all Dean could say in return, trying to smile back convincingly. 

Cas seemed unsure though. “Yeah?” 

Not knowing what he could say yet, he pulled Cas’s head back down to his shoulder and ran his palm up and down his friend’s back. 

“Yeah. I’m happy with this too.”

Only… how could he be? 

He’d just heard practically what he’d been wanting to hear yet the complete opposite too. Cas’s feelings had change too but he was willing to stay how they were just in case Dean was too scared to give him more? 

It was up to him now. 

He laid in bed wide awake as Cas slowly drifted off but Dean’s mind wouldn’t calm down. Despite wanting to shake Cas awake and confess it all, negative thoughts started to smother him. 

The fact that Cas would let himself settle for just this, for just some guy who hid them in a dorm room and didn’t have enough balls to let the world know he had the most awesome man beside him. The fact that Cas didn’t even ask to have more for himself when he deserved everything and more. It made Dean angry that Cas didn’t already know how much he was worth. That this—whatever this was, relationship or not, was nowhere near as great as it could be. It wasn’t enough and Dean wouldn’t let Cas believe ‘enough’ was adequate. 

It broke his heart that Cas would just do what he thought Dean wanted and let himself go on with rolling around in bed and never hearing that he was wanted, and desired, and _loved_ in a way that Cas desired. 

Dean suddenly felt completely inadequate at being able to make Cas happy. And it was pitiful that Cas had to resort to settling for someone who couldn’t get the courage to just say how he felt when he had the chance. 

He was so fucking angry at himself because now he knew Cas wanted this too but he couldn’t fucking do that to his best friend. Would he ever be able to get the courage? Would he ever be able to outright say that he wanted to mix their lives up so fully that he was willing to change any and all of his future plans just to stay by Cas’s side? 

He felt it all. He felt it all so deeply but he couldn’t fucking say it yet. 

It had to be because he was broken. Why else wouldn’t he have already jumped at the chance to make the angel in his arms officially his? 

He was always going to just be broken. His childhood made sure of that. 

How could he let Cas be with someone like that? Dean was always going to be a mess. He had the best thing that could ever happen to him and he was still scared of it. And to make it all worse he would always have to struggle with his problems… his past, his nightmare, the depression he sometimes fell into. 

It wasn’t fair! It wasn’t fair to Cas to make him deal with someone like Dean even if Dean managed to pull himself out of this. He’d eventually just be sucked back in like he always was. 

And even if Cas could deal with it. Why should he have to be with someone who could hardly get out of bed sometimes? Why should Cas be with someone he’d always have to take care of and worry about and baby? Why should Cas be with someone who was a giant coward when it came to his feelings?

Dean was a lot of things, but he wasn’t selfish enough to let Cas settle for him—for this.

So, he did what he did best. He pushed Cas away.

**Notes for the Chapter:**

> I hope you all didn't dislike this one too much! And I hope I wrote Dean's thought process decently. 
> 
> I am sick right now so I'm not sure how I feel about this chapter as a whole and I worry it wasn't as well edited as it could be but I didn't want to wait another week to be able to post it. If I choose to go back and edit I will add a note to the beginning of the next chapter. I hope to have it up in 2-3 weeks (hopefully sooner but I have a couple bangs to work on). 
> 
> Thank you to everyone who has been following along! It'll be a bit more bumpy the next chapter (or two) but there is a happy ending.


	17. March 3, 2018

“What happened? Cas? What’s wrong?” 

He hadn’t realized he’d walked himself all the way to Hannah’s until her hands were on his face, forcing him to look at her. Her eyes were scanning his face frantically and it was clear she was shocked to see his red-rimmed eyes and tear-soaked cheeks. 

He wasn’t a crier. He didn’t cry. He teared up when a sad movie came on or when he missed his dad but he didn’t ever cry over anything. Until now. 

What followed the most unbelievable night of his life had been some of the most heartbreaking days of his life. 

The morning after Valentine’s day, after the night he got to feel Dean’s body and mouth all over his skin, the night Castiel had finally worked up the courage to tell Dean he felt more for him than just friendship, he’d woken up alone on their futon. 

He had smiled against the pillow, convincing himself that maybe Dean had woken up early and gone out to get them some breakfast and would be back soon but when an hour had passed, then two, and Dean hadn’t returned, Castiel started to doubt himself. He eventually realized that it was Thursday and Dean was probably in class but when four o’clock, then five o’clock showed up and Dean still hadn’t come home, Castiel knew something was wrong. 

He’d put off texting his roommate as long as he could, but with his gut telling him something was off, he couldn’t resist sending a ‘are you on your way home?’ text. He even called thirty minutes later but Dean didn’t answer. 

Dean was running and Castiel couldn’t even pretend that it wasn’t his own fault. 

He’d thought he was being brave in telling Dean how he felt. He thought that maybe Dean would get the courage to tell Cas that he wasn’t cool with how things were and that he too had feelings and they should maybe give this a real shot… 

He hadn’t been brave at all apparently, he’d just been stupid. 

It was dark outside by the time Castiel realized that he hadn’t gotten out of bed all day. With that knowledge he dragged himself out of bed and spent the next four hours fixing their dorm room and leaving no evidence of their previous night. He had the overwhelming need to make sure their dorm wouldn’t offend Dean or make him any more uncomfortable than Castiel already had so he searched high and low, sorting their clothes that had gotten mixed up, putting back blankets and pillows they’d dragged off their beds, and making it look less like they’d mixed up their day to day lives in a way roommates don’t do. 

Late that night, after he’d fed himself, showered, and gotten back into pajamas, Castiel crawled into his own bed for the first time in who knows how long. It felt so wrong. He didn’t understand how a bed he’d slept in for so long before he and Dean started anything could feel so wrong but now his head was facing the wrong way and the mattress didn’t hug him the right way and his blanket didn’t feel as soft… 

He tried to let himself hope that Dean would come in through the front door and would spill all of his feelings—that he’d tell Castiel that he’d freaked out for a little but he realized that he felt the same way Cas did. 

It was possible right? 

Despite the twisting in his gut that screamed that he’d lost Dean for good… he wanted to be right about this. He wanted to believe that Dean wouldn’t end things so suddenly and that they would make it all work. 

His gut ended up being correct. 

He pretended to be asleep when Dean had snuck back into their room at eleven-thirty at night before finally succumbing to a restless sleep, only to be woken up at five-thirty to the sounds of Dean trying to stealthily pack his backpack up.

It felt like a slap in the face. To know that he was so unwanted that Dean had to resort to sneaking around to avoid having to speak to Castiel… it made him want to cry. 

The pain of it turned into anger and he realized he wasn’t going to let Dean walk out of there without saying something. Cas needed to know why Dean felt he had to do this, why Dean couldn’t let him down like a normal person would instead of running and hiding. So, he sat up in bed and flicked on his lamp. 

Dean had looked like a deer in headlights and it was only a matter of time before the man ran out of their dorm without a word so Castiel came out and asked, “Where’re you going?” 

He could almost laugh at how panicked Dean looked from being caught but his heart was aching to much. 

“Uh, I just—I was going—” 

“You’re avoiding me,” Castiel acused, knowing by the clench in Dean’s jaw that he was correct. 

His friend shouldered his backpack and pointed his thumb towards the door. “Look, I’m just gonna—” 

“What did I do?” Cas pleaded. 

He was angry and confused but it came out sounding broken and pathetic. He just didn’t understand. He didn’t understand why Dean would avoid him. Even if Dean didn’t feel comfortable knowing Cas had feelings for him, they were still friends before anything else. He should know that Castiel wouldn’t force himself on Dean just because he had confessed his feelings. 

It was a complete one-eighty from where they had been on Valentine’s day. How was it possible for the dynamic to shift between them so dramatically this quickly? 

Dean couldn’t even look in Cas’s direction. 

“Nothing,” the green-eyed man mumbled. 

“You’re lying,” Castiel argued. He could hear how emotional he sounded but he didn’t care. He was hurt that his best friend was pulling away and he had no idea why. “Everything was good and now you’re avoiding me.” 

There was look on Dean’s face, one Castiel had never seen before. He couldn’t explain it but he wanted to reach out to Dean and hold onto him for dear life. 

His friend shut his eyes and shook his head. 

“You didn’t do anything, Cas.”

“Then what is it?” 

“I just…” Dean looked at him, his bottom lip between his teeth, and sighed heavily. He looked tired and frustrated and Castiel knew he was just making it all worse but he had to know. 

“I don’t think we should do this anymore,” Dean said. It come out as a whisper but it shattered Castiel all the same. 

Tears rushed to his eyes and he could hear them in his voice as he asked, “Why?” 

“We… we took things too far.” 

Like a pathetic child trying to hold onto their favorite stuffed animal despite it being old and raggedy, Castiel refused to believe that the intimacy they shared was anything less than perfect. 

“No we didn’t.”

Dean turned away and his shoulders tensed up. “We did and we should end it before it gets too messy.” 

He wished he could’ve held it in but he choked on his sob and prayed that this was some sort of bad dream. Things weren’t supposed to end between them like this, not when Castiel hadn’t seen it coming. It didn’t make any sense and it hurt. 

“So now what?” He asked through his tears. “We can’t even be friends? You’re just going to leave and stop speaking to me?” 

Dean’s eyes were big and sad which didn’t make any sense. 

“We’re always going to be friends,” the other man insisted. “I just need some space for a while.” 

“How?” 

“We’ll keep to ourselves. Live our own lives.” 

Castiel had to swipe more tears away. He didn’t even know what his life looked like without Dean. How was he expected to just go on pretending like the most important person to him didn’t exist? 

“You can’t be serious.” 

As Castiel lost all his dignity and continued to break down, a wall built up around Dean and the man’s expression completely closed off. He looked at Castiel coldly. 

“I don’t know what you want me to say. We agreed that if either one of us said we should stop, we would stop, no questions asked.” 

He should’ve respected Dean’s wishes but he didn’t want to! He didn’t want this to be over already because he wasn’t ready. 

“But that was before…” 

Dean cut him off. “No questions asked,” he said sternly. 

“Don’t do this,” Castiel pleaded once again. 

Dean shook his head like he didn’t want to hear it anymore. Like he didn’t care. 

“You got your experience. You can go use it now.” 

“Dean.”

“I’ll be back eventually,” Dean stated, already walking away. “Don’t wait up.” 

“Dean, please.” 

When the door has clicked shut behind his best friend, Castiel had fallen back into his pillow and cried. He knew without Dean having to say anything that he had been the reason for this all getting fucked up. He shouldn’t have said anything! He should’ve let it all go on how it was because now he scared Dean away and broke up the single best friendship he’d ever known. 

He cried on and off all day in his bed before he couldn’t take the loneliness and found himself here, at Hannah’s doorstep, worrying his other best friend to no end. 

“I… I had a falling out with… with the guy,” he got out through his cries. 

“Why? What’s happened?” 

“He… he didn’t want to continue with our arrangement.” 

He expected to have this conversation months ago, way back at the beginning when he was still so unsure if Dean was serious about helping him. He thought he’d just tell Hannah, with a shrug, that it didn’t work out and he’d go back to being friends with Dean like nothing happened. But now? 

He’d gotten in way too deep and there was no coming back from it. 

“What?” Hannah asked sounding shocked. “You’ve both been so happy. Why would he just end it? Did you have a fight?” 

“No we… we were fine,” Castiel replied, his heart in his throat. “Everything was fine. I don’t know… I don’t know what happened.” 

He was ushered into Hannah’s, thankfully empty, dorm room and sat on her desk chair. 

“Did Dean say something?” She asked. “Did he give you any reason?” 

“No he… he just said that I’d learned everything I needed to know and I should go out and hook up with other people now.” 

He let Hannah pull him into a hug for a little bit, allowing her to comfort him as best as she could. 

When she pulled back she looked at him with a big frown and understanding eyes and said, “Cas, just go back and talk to him. I know him as well as you do, he’s probably just freaking out about all this.” 

That’s when he realized, “Wait… what do you mean you know him? You don’t even know his name.” 

To her credit, Hannah didn’t even roll her eyes. She looked at him and simply explained, “Honey, I’ve known it was Dean this whole time…” 

Castiel’s heart beat in his chest heavily, “I just—I was confused…” he tried to back track. “I didn’t hear you say—“ 

“Cas, I know its Dean.” Hannah said more firmly. “You don’t have to lie.”

“How?” 

He felt like an idiot. For lying to her, for being so obvious she would figure it out, and for outing this secret he swore he’d keep. 

But Hannah was the least judgmental person he knew and looking back he wishes he would’ve told her just to have someone to confess everything to. It might’ve made this all hurt a little less as it came crashing down around him. 

“I wasn’t sure at first,” Hannah explained, “but some of your stories weren’t adding up. Especially when I’d ask you where Dean was during some of your ‘hookups’ and you’d say he was at Benny’s but… I knew it wasn’t true because _I_ was with Benny then.” 

Hearing that was enough shock to momentarily take Cas’s mind off his sorrows. 

“Benny?” 

“I’ll tell you about it later,” she replied, he cheeks flush. “First I want to know if you’re okay.”

It wasn’t something he knew how to put into words so he diverged the question. 

“You knew I was lying and you didn’t say anything?” 

“I know you. So I knew you probably made a promise to Dean and I know that you’d never break a promise to him.” She squeezed his forearm and asked again, “Cas, are you okay?” 

“Not really.”

* * *

He spent that weekend with Hannah, laying in her bed as he told her everything that had happened from the start. He confessed everything to her, stopping every so often to get his tears out when his emotions hit him too hard. He had been so sure Dean felt something for him in return, especially on Valentine’s day. There was no doubt in Cas’s mind that they had made love that night so why did Dean want to just throw it all away? 

Maybe he cared about Cas but his feelings weren’t as strong as Cas’s were and that scared him? 

Maybe he thought he cared about Cas but going that far with him, sucking Cas’s dick and coming inside of him… maybe that had been too much for Dean and he realized he didn’t have feelings for Cas in that way. 

All Cas knew was that he was staying in Hannah’s room as long as the women’s dorm advisor would let him, and he was only staying in his own room when it was absolutely necessary. At least, that was until Becky, Hannah’s room advisor, developed a soft spot for him. Most advisors only let it slide every so often when boys tried to stay the night, which is why Castiel had gotten away with it on a few drunken nights, but Castiel practically moving in and staying over most nights and weekends too—he was lucky Becky was turning a blind eye. 

He didn’t think he could handle being alone in his dorm with Dean without the excuse of class to run away to. 

They hadn’t talked in two weeks. Two full weeks of avoiding looking at one another, leaving at least five feet of extra space as they navigated their room, and refusing to ask for help if something was lost or misplaced, it was excruciating. 

Castiel had never imagined heartbreak to feel so awful but every movie, book, show, or song hadn’t been lying about the pain it caused. At least he’d finally stopped crying over it. 

Mostly. 

“It’s Saturday. Wanna go out and get so drunk we forget about stupid boys?” Hannah asked, as the two of them laid on her bed. She’d wound up as his big spoon, and though it didn’t feel as comforting as Dean’s arms had, he appreciated how much she was caring for him. 

“You don’t have a stupid boy,” Cas argued back, knowing full well things were going really wonderfully for her and Benny. 

“Yeah but he could be some day,” Hannah pointed out. 

Cas chucked. 

“True.” 

“Wanna get drunk anyway?” 

It didn’t sound like the worst idea. It probably wasn’t the healthiest coping mechanism but it was only one night and would probably help to get his mind off of it at least for the night. He was so tired of feeling sad about himself all hours of the day. He was so tired of bringing Hannah down as well. 

“Yes please,” he confirmed determinedly, moving to sit up so he could get ready. 

Forgetting about stupid boys wound up meaning Hannah and Castiel meeting up with Benny at the dive bar by school after spending far too much money on tequila shots at the previous two bars they’d gone to. 

The night was going surprisingly well. He was having fun and he was happy to see Hannah and Benny looking happy together. 

But he had to admit that it made him a little jealous too. 

He tried to not let it show that most of his thoughts were still about Dean. 

He would’ve given anything to just know that Dean was _his_. He didn’t need the PDA or the knowledge that other people knew they were a couple. He would’ve been happy keeping it a secret as long as Dean needed. It would’ve been worth it to know that Dean wanted to be with him, even if he wasn’t ready to tell people. It would have made all the difference to be able to crawl into Dean’s arms because Dean wanted to hold Cas—or for them to kiss all night because they were together… 

But Cas was never going to have that. Not with Dean and probably not with anyone else. If this was what losing love felt like, he wanted no part in it ever again. 

He hoped Hannah would have more luck with Benny. And really, he knew she would since Benny was a good guy and he actually wanted her back and, in Cas’s experience, that made all the difference. 

He wanted to give his friend as much time with Benny as he could, since she’d spent the past few weeks taking care of him like the loser he was. It was his way of saying thank you for being so amazing. 

He excused himself to go to the restroom again and let her know he was going to grab a couple more drinks—just because. He wasn’t feeling great still but he was worlds better than where he’d been when it had all crumbled around him. He was even on the good side of too tipsy that things felt a little lighter. 

So of course, things had to go to shit. 

It was on his way back from the restroom that he noticed him. 

Castiel figured it was the gravitation pull that always drew him in, making him realize that Dean was in the bar, standing on the far end where he wouldn’t notice Castiel. It knocked the wind out of him to see the other man there, despite seeing him at home every now and them. It might’ve just been the fact that clearly Dean was already moving on his with life post his and Cas’s arrangement and that hurt something fierce but seeing Dean with his arm around Lisa…. 

If Castiel thought he was broken before, _this_ was going to be the end of him. Obviously, Dean would bounce back and find other people—fuck, he probably had already been with other people since they ended things—but actually seeing it? That was something Cas hoped he could avoid. 

Yet, there, clear as day, Dean leaned into Lisa’s face looking like a man starving of hunger. It was before Cas had the wits about him to yank his eyesight away that he saw the man he loved lean forward and kiss a woman that was without a doubt perfect for him. The type of woman Castiel always expected Dean to go for—beautiful, funny, kind; with breasts and a vagina that he could never ever offer. 

His breath caught as his chest constricted and he felt himself fumbling towards the door, ready to get the hell out of there and go _anywhere._

“Cas? What’s wrong?” Hannah asked, suddenly in front of him, looking worried and a little frightened. 

Castiel hadn’t realized he’d started crying until the tears were dripping off his chin. What a sight he probably looked. 

Fuck tequila. 

He must’ve glanced Dean’s way since Hannah was suddenly glaring at the man across the bar who seemed to be looking at them in return. 

“What a fucking dick,” She spat, more anger in her voice than Castiel had ever heard. He didn’t argue when she started to turn him away from where he could still see Dean, leading him out the door. “Let’s go home.” 

“Not a dick—” Cas cried, unsure why he was even saying it but the liquor was making him loose lipped. “Can kiss who’ver he wanna.” 

“He hurt you so that makes him a dick.” 

By the time Hannah had gotten him tucked into her bed, Castiel was mostly a mess of hiccups and small sobs he couldn’t seem to control. The room was spinning from the amount of tequila he’d consumed and his head was throbbing from the pain of crying, and he knew without a doubt he would feel it all five times worse in the morning. 

He didn’t want to imagine what the pain of realizing Dean had moved on would feel like in the morning if it already hurt so damn badly. 

“S’my fault.”

And it was. That was the only thought that kept circling around in his mind. If he wouldn’t have said anything, he could still be with Dean right now. His friend wouldn’t have gone off and put his hands on someone else. He wouldn’t have been kissing someone else because Castiel would have been satisfying his needs. If he wouldn’t have said anything he would still have Dean!

He hated that he couldn’t stop crying about this. He wanted to stop feeling so damn pathetic crying over a boy but he’d given all of himself away to Dean and he didn’t think he could handle not having his best friend in his life anymore. Even if Dean said they’d always be friends, Cas knew those were just words. 

“No, honey, it’s his fault,” Hannah replied, stroking his hair. “He knew what he was doing taking advantage of you.” 

Castiel shook his head because as much as he was hurting, he refused to let her believe Dean was a shitty guy. 

“He’d wouldn’t never do that. He’s my friend,” he slurred around his whimpers. Bless Hannah for dealing with his inebriated emotions. 

“If he was your friend, he wouldn’t have slept with you and then thrown you out.” 

He understood how Hannah could think that but he didn’t have the heart to explain to her that it was truly all Castiel’s fault. He was the one who backed Dean into a corner and made the man agree to be Castiel’s sexual awakening. It was Castiel who kept pushing the boundaries and asking for more and more of Dean despite knowing that Dean wasn’t interested in men. It was Castiel who blabbered all about his feelings even though he knew it would put Dean into an even more uncomfortable situation and so when it came down to it, it was all on Castiel. 

“I got too love for him,” he explained wobbly. “I’s my fault. Wasn’t supposed’a love’im.” 

“Castiel, you loved him even before you two slept together.” 

He supposed that was true. Dean had been the center of his universe long before now so it made it even worse to lose what they had. 

“Love’im more now,” he confessed. “S’much my heart hurting.” 

“You’re going to be okay.” 

In theory it was true despite the fact that his body, mind, and heart said he’d probably never feel okay. He hoped it was just the alcohol talking. 

At least Dean would actually be okay. Castiel couldn’t even hate him for any of it. Dean ended things when it crossed the line and now the man was able to go after what he wanted without Castiel being in the way. 

“So’s Dean. He’s Lisa now.” He tried not to sound bitter but the tears flowed freely despite his insistent swiping at his eyes. 

He must’ve looked as much like the wreck he felt because Hannah was looking at him with the most pitying eyes. 

“You need to get some sleep.” 

“Why’m I not good’nough?” He asked as he burst into tears. He had no idea where the outburst came from but he’d forever insist that it was the culmination of alcohol, lack of sleep, an impending hangover, and the volume of how much he missed Dean that suddenly poured out of him. “Why can’t Dean love me too?” 

“I don’t know honey. It’s not fair.” 

“Just want’im happy. Wanna be ‘is frien’igan.” 

That’s all he wanted really. Even if Dean would never have a romantic feeling in his body. Even if Castiel never got to sleep in the other man’s arms again. Even if he never got to know what it felt like to be completely one with Dean inside of him ever again—he’d give it all up to just have a best friend. To have the person he could go to for anything. To have the person who understood him like no one else, who cared for him and was willing to help him navigate through this part of his life. He just wanted Dean to not look at him and be disgusted by what they did. 

“You’re so good. Dean doesn’t know what he let go of. It’s really his loss.” 

Castiel couldn’t disagree more, though he didn’t voice it. He wasn’t much of a loss at all. He was certain Dean didn’t even miss him.


	18. March 14, 2018

**Notes for the Chapter:**

> We're almost to the end! BUT if you haven't already noticed there will be a part two. :) Right now the plan is just for a timestamp/epilogue but I really love these boys so it might be expanded a bit more. 
> 
> That being said, Dean is in the thick of his depression in this chapter and he starts to work through it if that is something anyone wants to have a warning for. There is no self harm, thoughts of self harm, or anything I believe could be triggering to anyone. However, if I'm incorrect and I wrote something incorrectly or wrote something that could benefit from a warning, please let me know.

They hadn’t talked in a month. One month, to the day. 

Apart from the awkward apologies when bumping into one another in their dorm rooms, or the half-hearted hellos when they passed by each other, Dean and Castiel hasn’t said a word since Dean ended things. 

It felt like drowning. Every day he couldn’t breathe and every minute he spent not hearing Cas’s voice, not seeing his friend’s smile, made him hate himself even more. And he hated himself thoroughly these days. 

Breaking Cas’s heart was the worst thing he’d ever done. Seeing the tears streaming down his face… Dean had cried in his car for an hour cursing himself for ever letting Cas get so close to him when Dean knew he was poison. He didn’t blame Cas for avoiding the dorm room at all cost, even after Dean had finally given up on avoiding it himself. 

It’d been miserable trying to hide out in the library or at coffee shops during the day, hanging around until he had to drag himself to classes he hardly cared about anymore. Eating dinner in the corner booths of fast food restaurants, alone, hadn’t felt too great either but he knew he deserved it. He’d fucked up so much. 

He never should have agreed to help Cas in the first place because then they would’ve avoided this heartbreak but the thought of never sharing what he and Cas had made him ache in a way he didn’t have words for. He didn’t regret it. How could he when it was the happiest and most whole he’d ever felt? Being with Cas had opened up his eyes and shown him everything he used to think he didn’t want but now didn’t know if he could live without. 

He didn’t want to live without Cas and now that he was, he knew how big of a mistake he’d made. He regretting ending it with every fiber of his being. He regretted walking out that door and letting Cas believe he wasn’t completely desired, loved, and adored. 

He shouldn’t have done it and every day he thought of falling on his knees at Cas’s feet and begging for forgiveness but he knew it would be hopeless. He fucked up too badly and hurt Cas too deeply. He didn’t even want to be forgiven. 

Why would Cas even want him now anyway? After Dean cast him aside so heartlessly? 

And then knowing what Cas saw… 

Fuck! He was such an idiot! He should have just hung out at McDonalds again instead of giving in to his loneliness and deciding one drink at the bar would make him feel better. And running into Lisa as he was walking in? That should’ve been his first red flag. 

He tried to act like he cared about what she had to say. He tried to play it cool and make her think he was interested because he figured a distraction would help with the hole in his heart, but when he moronically decided to kiss her just to see if it would do anything, all he tasted was regret. 

And to top it all off, looking up to see Cas’s face shattered… Dean couldn’t get the sight out of his mind. 

It plagued him daily. Over and over he kept seeing Cas’s tears—the ones on the morning Dean ended things and the ones at the bar. Making Cas cry felt like the ultimate failure. He wanted so badly to be a good memory, one Cas could look back on and know he was treated well and cared for yet Dean wound up hurting instead. He knew Cas wouldn’t forgive him and Dean hoped, for Cas’s sake, he wouldn’t. 

He wasn’t doing well. 

That much was obvious. 

Getting out of bed wasn’t an option anymore and going to class didn’t cross his mind. 

His nightmares were back too. Blurred images and muffed voices of screaming, of hearing how worthless he is, of small motel closets that were never hidden enough to keep the monsters away. 

“Dean?” 

His hand hit a solid figured and he jerked back, slamming himself against the wall. It was dark all around him and it took a few rapid breaths to realize he was in his dorm room. 

“Dean? Are you alright?” 

It was Cas’s voice next to him. Cas’s warm hand on Dean’s arm that had presumably slammed into Cas’s stomach due to his flailing. 

The last thing he wanted was for Cas to see him like this. So damn broken. 

“M’fine,” he lied, pulling his arm back and curling in on himself. 

“You were having a nightmare.”

Dean didn’t want to know what he must’ve been calling out or what pathetic noises he made to make Cas act concerned, but knew he was a waste of Cas’s time and energy. 

“I’m fine,” he lied again, trying to keep the wetness in his eyes from spilling over. It was a small mercy that the room was still dark and he could only just make out Cas’s silhouette, at least the other man wouldn’t see how much of a wreck Dean was. 

He would give anything to have Cas crawl into bed with him right then and wrap him up tight. Even having Cas standing near his bed, Dean could still detect Cas’s scent and he ached to fall asleep to that smell surrounding him. 

But when Castiel asked, “Do you need anything?” Dean didn’t tell the truth. 

_You,_ his mind screamed as he heard himself say, “Just leave me alone.” 

He hoped Cas would argue with him and refuse to leave his side, fighting away all of Dean’s demons with the comfort of his arms. 

Dean wound up alone in his cold bed, exactly as he was meant to, without the man he loved beside him. 

Poor, broken Dean.

* * *

The days started to blend into one another. 

Dean wasn’t certain on the last time he’d spoken to anyone besides a very tearful phone call with his brother about a week ago. He’d blown off his friends, wasn’t going to class, and started to ignore any call that came in. He knew he needed help but he was too damn exhausted to want to bother. 

To top it off, Cas seemed to be around more than before. 

Every morning Dean was waking up to Cas obnoxiously banging into things and loudly opening and shutting their bathroom and closet doors. Dean didn’t have the energy to tell the other man to shut the fuck up and let him sleep. He even didn’t have the energy to pull the covers back over his head. 

As much as he craved Cas’s proximity, being this dark and twisty made him wish Cas would go away. He hated that Cas was seeing him like this, probably judging him for being such a sad sack of shit and relishing in his freedom from Dean. It made it all worse that Cas had taken to asking, _“Do you need anything?”_ every fucking day before he took off to who knows where, and every night before bed. 

It was just a painful reminder that Cas no longer had a place in his life and Dean wished he didn’t have to say no every time. 

Day in and day out he kept telling himself he’d be fine. _Soon,_ he’d say. _Tomorrow,_ he’d promise. The fog was supposed to clear any day now and he’d get over this but so far that day hadn’t come. 

Most of the time he was alone now, drifting in and out of sleep or staring at the time on his phone and telling himself he’d get up and shower in five minutes… or fifteen. His diet was mostly instant ramen and small cups of microwavable macaroni, and he knew he wasn’t drinking enough water but that meant he had to get up to piss more than he had energy for. He felt so stupid for feeling so shitty but he couldn’t imagine crawling out of it. 

He felt his phone buzz for the third time that morning and sent the phone straight to voicemail before checking the notification telling him it was his mom calling yet again. Just like every time he looked at his phone, his chest caved in as he looked at the background—still a picture of Cas with the stupid crocheted bee Dean got him for Christmas. Every day he told himself he should change it but the second the thought crossed his mind he shoved it away, not wanting to give up the only way he had to look at Cas’s smiling face still. 

He was so stupid. 

While he stared at the picture, wondering if he’d ever be the one to make that smile happen again, a text popped up on his screen. 

**Mom:** Answer the phone or so help me I am taking the next flight out there. 

The alarm sirens in his mind started sounded (a little too late, let’s be honest) and Dean’s heart thrummed in his chest as his mother’s next phone call came in. 

He did _not_ want to speak to her right now but he knew Jody was a woman of her word and would be at his doorstep by nightfall if he didn’t answer. 

Dean’s hands shook as the phone started to buzz. 

“Hello?” His voice was hoarse from the lack of use and he had to clear his throat a few times before he could get the word out correctly. 

“Dean! Why haven’t you been answering?” There was a frantic quality to Jody’s voice and Dean had to think back to how many of her calls he’d actually been screening. At minimum a week’s worth. 

“I was sleeping,” he lied. 

He didn’t imagine for a second that she’d buy it, she was his mom after all. 

“Honey, what’s wrong? I know something’s wrong. I can feel it in my bones.”

He wanted to be strong and tell her that nothing was wrong. To hold it together and sound like he wasn’t empty inside but he just wasn’t strong enough. Everything he’d been holding onto for weeks clawed its way up his throat and it wasn’t long before he was choking off a sob. 

“Mom…” 

“Honey, talk to me.” 

He wasn’t sure why hearing his mom’s voice brought out every ounce of emotion he’d been holding back on but he allowed himself the chance to get it all out, listening to his mom guide him on breathing, saying every soothing thing she could just like when he was little. He wasn’t certain how long he broke down but when he did catch his breath and managed to follow along to her instructions to breathe in and out, he was able to tell her: 

“Everything’s shit.” 

She didn’t try and tell him everything was going to be okay nor did she try and lighten the situation. They’d been down this road before, a few times actually, and his mom somehow always knew what Dean needed to hear. 

“For how long?” She asked him, probably already knowing the answer since Dean had been avoiding her calls for too long. 

He didn’t really want to admit to her that it’d been since Christmas break. 

“I don’t know,” he muttered, knowing she could hear the lie in his tone. 

“When was the last time you saw Pamela?” 

Dean actually had to think to answer that one. He’d grown up in therapy, he had to with his past, and it’d been something he kept up when he entered college, but he wasn’t sure the last time he actually decided to go. It had been a monthly thing but then senior year started and he just kinda let it go. 

“I don’t know,” he confessed, already feeling frustrated with himself. He knew better than this. 

He was half expecting his mother to say just that but she never would. His mom was the most understanding person on the planet and had never once made him feel bad for not taking care of himself properly. Instead, she helped. She took care of the things he didn’t feel like he could do yet because that’s the kind of mom she was. Which is why he wasn’t surprised when she asked, “Do you want me to call and schedule an appointment for you?” 

He knew if she didn’t do it for him, he probably wouldn’t bother calling. If he had a set date to see her, he’d be able to drag his ass out of bed and over to Pam’s office, but actually setting that up himself sounded like too much work. 

“Okay,” he agreed. 

“Have you been going to classes?” He knew from her tone she wasn’t judging him, just trying to gauge how he was doing. And not for the first time, he was so glad she chose to be his mom. 

“No,” he answered honestly. 

“Do you think you can email your professors?” 

“Probably.” 

He’d be lying if he said he wasn’t anxious about his final classes. He’d been doing so damn well in school up until this point that he was terrified of fucking it up so close to the finish line. He figured writing an email to explain what was happening wouldn’t be the hardest thing for him to do and he was sure if he asked, his mom would help him write it out so he could send it. He really, really didn’t deserve the people in his life but thank fuck that the universe gave them to him anyway. 

“Okay,” his mom said definitively, “we’ll take this one step at a time.” 

And that’s exactly what they did. 

His mom and dad both called him frequently throughout the days and checked on him, getting him to eat, to shower, to drink water, and to talk. He wound up going in to see Pamela a few days after his phone call with his mom and he and Pam worked out some next steps for Dean to take. His professors were more understanding than he thought they’d be, and after a few extensions and late assignments, he was close to getting back on track. 

He still wasn’t good. Sometimes he wasn’t really okay, but it wasn’t getting worse either. 

The fog did start to clear, blowing away more and more mental clouds every day until he didn’t wake up and immediately want to sleep an extra two hours. 

Focusing on taking care of his basic needs worked as a distraction to keep his mind off of how badly he’d screwed things up with Cas. He still missed Cas so deeply and thought about him constantly. The regret of letting go of what they had still cut him to the core but he knew trying to repair things between them wouldn’t work unless Dean worked on repairing himself a little more. 

Cas still asked daily if Dean needed anything and along the way Dean stopped just saying no. _‘I’m okay, thank you,’_ and ‘not right now but thanks, had become the only sentences he was brave enough to say to the other man, but it felt like a start. If anything, Dean wanted to at least be on good terms with Cas again. 

He didn’t really know what was going on in Cas’s life these days. It was still pretty heartbreaking to realize they’d once had their lives so entangled and knew each other better than anyone else yet now they were practically strangers. He wanted to change that and he wanted to change it badly. Every day the words _‘how are you’_ were at the tip of his tongue but he was too scared to ask. 

It would make sense if Cas hated him and didn’t want to speak to him. Dean had broken Cas’s heart and broken his unspoken promise to never hurt Cas. If Dean did ever work up the courage to try and talk to Cas like friends again, Cas had every right to shut Dean down and tell him to fuck off. It’d hurt like a bitch but it would only be fair. 

It was early April before Dean could finally get the words out. 

He’d just walked in the dorm after a meeting with his professor (he was definitely going to graduate as long as he kept turning in his missed assignments) and was feeling really good about the day. 

Seeing Cas studying at the desk, Dean just blurted out, “How was your day?” 

Cas startled a bit before looking up and asking, “Wha—Me?” 

The question made Dean chuckle under his breath. 

“There’s no one else here. So yeah, you.” 

Cas looked at Dean skeptically for a moment before the corners of his mouth turned up and he answered, “It—it was good. And yourself?” 

He was almost in awe that they were talking again that he almost didn’t answer but he caught himself staring. 

“Me too. It was good. A good day.”

Whatever gibberish came out of his mouth seemed to be an acceptable answer. 

“I’m glad,” his roommate replied. 

That was all Dean got that night but it felt good to have accomplished that much. He went to bed that night with a smile on his face and the hope of more baby steps between them.

* * *

Things probably wouldn’t ever fully go back to normal but every day was a lot easier to manage than before. 

Dean was able to take himself to the gym again and text the friends he’d been blowing off and let them know where he’d been. He still wasn’t up for hanging out with his friends as much as he once had but they seemed to understand. Benny had been the one to suggest they go to the gym together even though they didn’t talk much while there. It was helping. Every little thing helped and he felt himself getting better. 

Most days he was even able to work up the nerve to string together a few sentences to talk to Cas. It was mostly lame small talk like asking if Cas needed something from the store, or commenting on the rare rainy days, but it was still _something._ He didn’t dare hope that they would ever be best friends again but his goal was to at least make their relationship with one another cordial. 

He wondered daily how Cas was doing. What he was up to, who he spent his time with… if he was seeing someone else. It hurt to think about the possibility that Cas had already moved on but Dean knew how much a catch Cas was, it would be surprising if no one had already tried to lock the other man down. 

Dean couldn’t imagine himself ever really wanting to go back out into the dating world. The thought of hookups revolted him and he figured it would be a long while before he’d be able to move on. No one was ever going to compare to Cas, not by a long shot. What they had was something deep, even if they were never _really_ together; Dean had never connected to someone the way he had with Cas, emotionally or physically, and that wasn’t something he took lightly. 

He tried not to think about what things would be like if he had taken care of himself sooner when he started to notice the signs. Would he and Cas still be good? Would Valentine’s Day have given Dean the courage to tell Cas that he loved him and wanted to give them a shot? Would he be telling the world right now that he was Cas’s boyfriend and that he was the happiest he’d ever been in his life? It’s how he liked to think of it in his mind. 

It didn’t do him any good to dwell on _what if’s_ but he didn’t think he was brave enough to try and fix it and with the end of the year creeping up and graduation looming over them he felt like he was already running out of time. 

Bobby kept trying to encourage him to talk to Cas, trying to help Dean phrase his apology enough to at least earn Cas’s friendship back but the thought of rejection scared him away every time. 

Cas seemed to be doing well, spending time with friends, getting all of his school work done, and being generally happy. Why would he want Dean coming back into his life and messing it up for him again? 

But what if he was just waiting for Dean to apologize? 

He didn’t know what to do and he was scared it would eventually be too late. 

**Benny:** Dude Cas is so shitfaced. 

Dean sat up straight on the couch and read over Benny’s texts a few times. It was a Saturday night and most weekends Cas seemed to be off with friends. It wasn’t surprising to hear that Cas and Benny were out together but what he didn’t understand was why Benny thought he’d even have to tell Dean. 

_Dean:_ What? Is he okay? 

**Benny:** We’re all at Coles party and hes so drunk. Probably gonna get some tonight. 

If Benny knew what had happened between Dean and Cas, Dean would’ve thought it was cruel to text this to Dean but since he was reasonably sure Benny had been in the dark the whole time, he wondered if Benny was worried. 

_Dean:_ Is he okay? 

**Benny:** Seems alright to me

**Benny:** All over some nerdy dude. I think they hit it off 

Dean felt sick to his stomach and a whole lot like he was about to cry. He knew Cas was going to meet someone eventually but Dean wanted to be long gone before he had to watch it happen. Knowing he was the one who gave it all up by pushing Cas away was the hardest pill to swallow. He wanted to be with Cas more than anything but he gave up his chance and now someone else seemed to be closing in on it. 

He stewed in his thoughts for a while, torturing himself with images of Cas with another man. Of this mystery guy getting to see the way Cas smiles or feel the smoothness of his skin. It killed him to think that another person might get to put his lips on the curve of Cas’s neck or run their fingers through his hair. He couldn’t handle the thoughts of Cas experiencing things with someone who wasn’t Dean. 

A series of texts suddenly went off on his phone and Dean almost ignored them, not wanting to know what sort of unwanted information Benny was texting him now. But Dean was obviously a glutton for punishment because it took him only a minute to take a glance at his notifications. 

**Hannah:** Dean, did Cas go back to your place? 

**Hannah:** He left and I have no idea where he went. 

**Hannah:** He won’t answer his phone. 

**Hannah:** Let me know if he made it home please. 

His heart dropped. 

Cas was with someone else. 

Dean had no right to be jealous because Cas had never been his but fuck if it didn’t hurt. 

He let himself feel his pain for a while. He didn’t know how he was going to be around his roommate later and not show how destroyed he was by this, but he had to figured it out. He didn’t want Cas to feel guilty for moving on or getting out there and meeting new people, it had been what Cas wanted from the start. So Dean needed to get his shit together but he needed a minute first. 

**Hannah:** Dean? Is he home? 

_Dean:_ No but ill let you know if I hear from him 

He was under no illusion that Cas would come home that night. 

Heartbroken, Dean pulled himself off the couch and decided he would take a shower to keep himself from falling into bed and trying to sleep for twelve hours. 

He was on autopilot as he stepped into the running water and cleaned himself off before getting into his pajamas and sinking back down onto the couch. He figured watching some mindless TV would be a better use of his time than lying in bed, tossing and turning, imagining what some other man was doing to the person Dean loved. He knew he wasn’t going to sleep that night and if he did manage to doze off it wouldn’t be restful. 

About an episode into Dr. Sexy he thought he heard someone at his door. He paused the show to make sure he was hearing right and sure enough he heard the handle of the door being jostled. 

He got up off the couch and headed that way only to hear a few knocks before the handle jostled again. 

The short walk to the door he prayed that Cas wouldn’t be uncaring enough to bring the guy back to their place. He didn’t know what he would do. His heart was racing as he reached for the door handle, hoping he had the strength to deal with this. 

Taking a deep breath, he opened the door.

**Notes for the Chapter:**

> Thank you all for sticking with this slow burn! I know it's been frustrating, especially that I'm not posting every week now. I do hope you all still like where it's been going and will stick around. (Subscribe to the series so you can see part two once this is part is finished). 
> 
> For those of you who really dislike cliffhangers I'll give a few spoilers to ease your minds so stop reading if you want to wait to see what happens and stew in the angst until I get the last chapter up. :) I'm hoping to post no later than March 28th though I hope I can post sooner. 
> 
> ***Spoilers: Cas does not sleep with anyone else. He does not do anything physically besides kissing. He is alone when Dean opens the door but still pretty drunk.


	19. April 14, 2018

**Notes for the Chapter:**

> We're here. I almost can't believe it. These boys put me through it on this last chapter, refusing to listen to any idea I'd already had written and choosing to tell this ending. I really hope you all enjoy. I'll see you in the end notes<3

He was less drunk than he’d been hours ago but now that exhaustion had caught up to the endings of his buzz, the floor was definitely still moving underneath him. 

And he’d lost his keys. 

He was torn between waking Dean up or hauling himself back over to Hannah’s but the thought of walking across campus sounded awful. He was too tired and too wobbly on his legs to think it was a good idea. And he was already _home._

He must’ve been making too much noise because the door to his dorm room swung open and Dean stood before him looking so unfairly beautiful Cas could throw up. 

Two months. 

He lost Dean two months ago and it still ached like nothing he’d ever felt before. 

“Are you okay?” Dean asked, his voice sounding worried. 

“I’m a little drunk,” Cas answered honestly, needing to lean on the doorframe for support. “I think I lost my keys.” 

“Okay,” Dean said with a little too much force. “Come in. I’ll get you water.” 

It was still so _awkward_ with them now. He hated it. He hated it so much because they were Castiel and Dean. They were supposed to be a team. Best friends. They weren’t supposed to walk around each other like—like—he wasn’t sure what, but it wasn’t supposed to be like this. 

A mug of water—Cas’s favorite mug—was placed in his hands and he drank the liquid thirstily before thanking Dean for the kindness. 

“It’s no big deal. Oh—just make sure you tell Hannah you’re home. She’s been texting me that she’s worried about you since you weren’t answering.” 

Castiel pulled his phone out of his pocket and looked at his screen that had no missed calls or texts from Hannah. 

“What? She hasn’t called,” he said with a bit of a slur. “She has my location too. She knew where I was.” 

Hannah! That’s where his keys were. He handed them to her to hold in her bag. Which meant he was going to have to get those from her tomorrow. With a hangover. Fuck. 

“Oh. Then I don’t know what that was about,” Dean said awkwardly. “She sounded worried.” 

Cas sent off a text to his friend to tell her that he was home and fine, and ignored her phone call that came moments after and the three consecutive texts. He threw his phone towards his bed and got up to fill his mug of water again. 

“I’m fine though. Clearly,” he stated, doing a good impression of walking in a straight line. As he took a sip of his water, he looked up to catch Dean looking at him with an odd expression on his face. 

“Okay. Good,” is all Dean said before turning away from him. Castiel watched Dean begin to start picking up his side table and the clutter on the windowsill, effectively ending any and all conversation he and Cas could’ve had. 

It was fine though. Cas had gotten used to it, especially over the last few months where it was apparent Dean held no interest in talking at all. 

It worried him, still did if he was being honest, how little Dean was willing to speak to anyone. At first Castiel had just thought it had to do with their breakup—_falling out_—but then he started to notice that Dean just didn’t seem okay. Hannah kept telling Cas that Benny was worried about Dean not replying to his messages, and that’s when Cas decided he’d go back to their dorm a little more often and see if everything was okay. It didn’t take long for him to realize Dean was hardly getting out of bed. 

Cas would get home from class and his roommate would be asleep. He’d get dinner and Dean would still be asleep. He’d wake up in the morning and get ready for class and Dean would hardly stir. It started to make him very, very worried. He’d asked Hannah what to do but refused to listen to her advice when she said he didn’t need to be worried about Dean anymore and instead decided to text Sam and let him know Dean didn’t seem to be doing super well. 

Sam had obviously been worried and tried to get Cas to help, but between not wanting to step on Dean’s toes and still reeling from his broken heart, he’d done what he could. He made sure Dean’s favorite foods were still in the dorm, that they had enough water, and would secretly throw some of Dean’s clothes in with his laundry once a week. It wasn’t a lot, and he knows he didn’t do much to help, but it’s all he could handle. He got to watch Dean getting better, and know that at least when Cas couldn’t be there for him, that Dean had a family who could. 

What he didn’t expect was that the better Dean started to look, the more he started to talk to Cas again too. 

Cas had started to accept that he probably would never talk to Dean the same way they once had, that they would graduate college and go their separate ways and only ever be memories to one another. He wasn’t okay with it, he wasn’t used to it, but it was his reality and he’d accepted it. 

But then Dean was there, asking about his day, making sure Cas didn’t need anything from the store and the solid but fragile wall he’d been building up around his heart started to crumble. It started to hurt again. 

Cas started looking at the room they shared and remembering how it felt to feel wanted. He’d look at the couch and be transported back to the first time he got to touch Dean, or the hallway where he’d felt Dean’s hands trail across his back as they passed each other. He’d look at the bed and relieve every time Dean’s skin brushed against his or the way it felt when the head of Dean’s cock would finally breach his entrance. He missed the way all of it felt, how out of his mind he’d feel with lust while simultaneously feeling himself fall so completely in love—and quite frankly, he missed sex too. 

It was that thought that had him thinking maybe, _maybe_ he should just start hooking up. 

He knew he was never getting Dean back and that no one would ever compare to him. He figured that maybe the only way to get past the knot in his stomach and the feeling that he’d probably end up alone was to just get back out there and do something stupid. 

It’s how he got here in the first place, getting out there and striking out with a frat boy to end up doing something stupid like asking his best friend in the entire world to take his virginity… it was on brand for him, being stupid. 

Despite Hannah loudly disagreeing, and Benny (who’d figured out what happened with him and Dean through context clues) telling him that sex with a stranger wasn’t the best coping mechanism to cure a broken heart, Cas chose to ignore them both. He was convince if he just got it out of the way and slept with another person it would all be easier. 

He planned to let loose at the party the three of them were invited to. And his plan was to simply see where the night went. He did manage to let loose and drink more than he’d probably drank in months and he definitely didn’t hold back from trying to talk to any male who seemed even slightly interested in him. 

That’s when he met Aaron. He was goofy and scruffy but he kept telling Cas that he had incredible eyes and a nice smile and Cas thought he could do it. He thought that he could go back home with the man and strip down to nothing and sleep with him and it would be _fine;_ he would be _fine._

Only getting back to Aaron’s place and feeling the itch of his beard as they kissed and the softness of his small hands as they found Cas’s hip under his shirt…. He couldn’t do it. It was like his body viscerally rejected the touch of someone who wasn’t Dean.

He’d apologized profusely through his slurred speech and promised Aaron that it wasn’t his fault and then stumbled his way back to his dorm where Dean found him, drunk without keys. 

And now Cas was sitting woozy and dejectedly on his beanbag, watching some random show on TV and wishing he didn’t feel so damn guilty and miserable over the fact that he’d thought about being with someone else. He needed to move on. He couldn’t go on forever wishing he could be with Dean when Dean didn’t want him. 

He just wasn’t ready yet. Hannah was right. He needed more time to move past this and figure out where to go from here. 

“Was he good to you?” 

Cas startled a bit before looking over his shoulder. For a minute Castiel thought Dean was on the phone, since his back was still turned but the subtle tilt to Dean’s jaw meant he was listening for an answer. 

“What?” Cas asked with confusion. 

Dean still didn’t turn to him. He was facing away with his shoulders tense. “The guy you were with… was he good to you?” 

Dread filled Cas to the core thinking he’d been mumbling about what happened under his breath, but there was no way. There was no way his jumbled thoughts led to him telling Dean what happened. So how in the world did Dean know? 

His voice was hardly a whisper. 

“How’d you know?” 

Dean pushed back from where he’d been hovering at his desk and started tugging at the shirt he was holding. 

“Benny… he told me… he told me you met some guy and looked like you two hit it off.” 

Cas began to tremble not knowing how to response. Why would Benny tell Dean about this in the first place? It was no one’s business but his own what he did. And it infuriated him that he felt like he’d been caught despite not having done anything wrong. 

He didn’t know what he was supposed to say. All that managed to come out of his mouth was a feeble, “Oh.” 

Dean looked at him for a long while before he shook his head and started to walk away. Only, he didn’t make it far before he turned back to Cas and probed. 

“Did he… did he treat you good?” 

Part of Cas wanted to ask why it mattered but another part of him couldn’t get over how unbelievably dejected Dean’s voice sounded despite the forced smile the other man was trying to pull off. 

It was out of confusion and his belief that Dean was worried Cas picked another crappy guy, that had Cas answering, “He was kind, yes.” 

A mixture of expressions washed over Dean’s face before he settled on looking at Cas with a half-smile. 

“Good.”

They stared at each other for a moment before Dean took a deep breath and quickly turned away. The undeniable sadness in the room had Castiel getting up from the beanbag and standing awkwardly in place, torn between walking towards Dean and keeping his distance. 

Was Dean upset that Cas had met a guy? Was he upset because he thought Castiel slept with Aaron? Why was Castiel feeling completely unsettled by this? Why did he want to reassure Dean that nothing happened when Dean was the one who broke his heart and pushed him away? 

It didn’t make sense why he felt compelled to say it, but he heard himself say it anyway. 

“But nothing happened.” 

Dean turned back around. He looked confused. 

“What?” 

“Nothing happened with me and him—the guy,” Castiel explained. He felt irritated with himself for feeling the urge to even tell Dean this especially when Dean hooked up with someone else only weeks after everything ended with them. “Not that it matters… but nothing happened.” 

Cas shrugged his shoulders and moved over towards his bed. He pulled back the comforter, ready to jump in and ignore this conversation and the whole night itself. What did it matter if he slept with someone else? Dean hadn’t ever wanted him in the first place. It didn’t matter what Cas did. 

Only Dean kept asking questions. 

“You didn’t sleep with him?” 

“No,” Cas reassured with his back still turned. He didn’t want to look at Dean’s face right now. “We just… we kissed but that’s all.” 

Dean’s sudden intake of breath is what made Cas look back at him. 

“You kissed him?” 

“Yeah.” 

It was unmistakable how upset Dean looked by this news and Cas couldn’t for the life of him fathom why. _If_ Dean did care for him, he still had no room to feel this way since he kissed Lisa so shortly after they ended things. And _if_ Dean was upset about this, he _still_ had no right to voice it because he told Cas to go out and get experience with other people. 

Yet seeing Dean upset hurt Cas more than it made him angry. Especially when Dean’s face fell a split second before he shook it off and nodded his head, expressionless. 

“Okay.” 

It was infuriating to not know what was happening and why Dean was flipping in and out of his moods. Cas just needed to know what the hell was going on. 

“Why’re you upset?” 

In typical Dean fashion, the other man stayed closed up, immediately retorting with, “I’m not.” 

As much as Cas wanted to pry, there was nothing Cas wanted to say to _that._ If Dean wanted to refuse to talk about what was clearly upsetting him, then he was going to let the other man stew in his feelings and Cas was going to just ignore it because it wasn’t fair to him. 

He threw up his hands. 

“Fine.” 

Now fully aggravated, he shoved off his jeans and climbed into his bed, turning his back towards Dean and pulling the covers up to his shoulders. 

Cas wasn’t going to deal with this tonight. He’d done nothing wrong yet Dean was upset with him for something and was refusing to talk about it. What else was Cas supposed to do? 

It didn’t matter anyway since they weren’t even friends. Not anymore. 

But fuck, did he wish that wasn’t true. 

He wished they _were_ something to each other. That he could talk to Dean about why he was sad and fix it because he wanted to make Dean happy. 

He wished he wasn’t laying in his stupid bed with the man he fell in love with completely closed off from him. 

His wished this wasn’t how it worked out for him. 

“I just—fuck,” he heard from behind him. “It’s so fucking stupid, Cas” 

Cas didn’t dare turn over, in fear that if he did, Dean did would stop. With bated breath, he waited for Dean to say more. 

“I am upset and I swear it’s not your fault, it’s just because—”

For a moment Castiel thought Dean wouldn’t finish his thought since his pause lasted so long. He could almost hear Dean’s heart beating as the time passed. 

“It’s because I never got that,” Dean confessed in the softest whisper, almost too soft for Cas to hear. “And I don’t even know who he is but I _hate_ him for it.” 

Castiel stared at the wall for a little while, wondering how he was supposed to respond to that. He took a few deep breaths. 

His roommate was standing at the far end of the room looking devastatingly beautiful when Castiel sat up.

He’d known Dean for over three years and in that time, he’d never seen quite a look on the man’s face. In fact, Cas used to think Dean was the most emotionally strong person he’d ever known. In the years they were friends, he’d never seen Dean cry, get too angry or even flinch when something scary happened. He thought Dean just had it all figured out in a way Cas never could but this Dean in front of him was something else. His eyes were big and sad, his shoulders slumped, and Cas’s instinct was to comfort him until all the pain went away. 

And all Castiel could think was, _why?_

Why did Dean look this miserable over Cas kissing someone else? 

How did that make sense with everything that had happened the past two months? 

“You hate him? For kissing me?” 

If Dean was surprised by Cas’s question, he didn’t show it. 

His response tumbled past his lips immediately. 

“Yeah.” 

Cas could only stare at his former best friend, watching as the other man’s emotions tumbled through him. 

“But you never wanted to kiss me,” Castiel pointed out. It was the kicker to all of this. Why did it even matter if he kissed someone else if Dean never wanted to kiss him in the first place? “So why would it matter if someone else did?” 

He could see that his question stirred something in Dean because his roommate looked at him as if Cas had grown four heads. 

“I wanted to kiss you,” Dean explained. “But you never asked me to so I knew _you_ probably didn’t want to…” 

“I wanted to! How could you think that I didn’t?” 

“Well you never…” 

“You never did either!” 

Castiel didn’t know when he’d gotten out of bed but he was standing only a few feet away from Dean, his heart pounding in his chest because he couldn’t believe what he was hearing. 

In all their time together Dean had just been waiting for Cas to ask him? He hadn’t already known from the way Castiel couldn’t stand to be away from him and always needed to be touching Dean that Cas wanted more than what they had? He hadn’t known from the nights Cas clung to him, and refused to go to his own bed because he craved sleeping next to Dean? He hadn’t figured it out by the way Castiel _confessed_ how his feelings had changed between them that Castiel wanted to kiss him? 

This would’ve been the best news of his life two months ago. He would’ve thought that he was on top of the world but they were here. 

And Dean seemed to understand that as well. 

“I know,” Dean sighed heavily. “I’m sorry. But it doesn’t matter anymore.” 

“Of course it doesn’t,” Castiel mumbled, his heart shattered yet again. “I stopped mattering to you months ago.” 

He didn’t want to have this conversation anymore. The fact of the matter was that they’d had something between them, something amazing and mutual but now they didn’t and Castiel didn’t get to be a part of Dean’s life anymore. 

“Cas—” 

“No. I don’t want to hear it,” Cas shouted. He could feel the emotion thick in his throat and he was certain he was going to start crying. How dare Dean bring this up when Castiel was trying to get over him? How dare Dean make Castiel feel so shitty for trying to move on when Dean had done the same thing months ago? How dare he stand there and tell Cas that he’d wanted him too when there was nothing they could do about it now? 

Dean threw them away and Cas still didn’t even know why. Especially now that he knew Dean had wanted to kiss him too! 

“Actually I do!” He heard himself declare. “I want to know why you just stopped caring. Why we couldn’t even be friends anymore even when I begged you to not do this.” 

“I didn’t stop caring,” Dean said with force. But Castiel couldn’t believe it. He turned on his roommate and glared at him, the tears now starting to form in Cas’s eyes. 

“I didn’t!” Dean insisted. “I swear, Cas. I still cared. I still _care._” 

“Then why?” 

“Because I’m broken!”

The force behind Dean’s words punched Castiel square in the gut, bringing him back down to reality. He could see it in the dejectedness in Dean’s eyes that the other man truly believed what he was saying. 

Castiel watched helplessly as tears started pouring out of the other man’s eyes as he explained, “I was a wreck and I couldn’t stop it and I thought it would be easier if you didn’t have to deal with me being broken too.” 

“You’re not broken.” 

“Cas—” Dean cried, “I’ve only _just_ managed to get my head above water. I _literally_ have to talk to my parents all day to make sure that I’m functional and not forgetting to brush my teeth. I’m not okay. I wasn’t okay coming back from break and I—I didn’t know what to do.” 

Castiel felt like an idiot for not having noticed. Dean _hadn’t_ been like himself but Castiel had hardly realized. How could he have gone weeks without figuring out that something was wrong with the man he spent every moment of his days with?

“Why didn’t you tell me?” 

Dean shrugged and swiped at a few stray tears. 

“I wasn’t ready to admit to _myself_ that I had a problem. And by the time that I was, I’d already pushed you away.” 

He could hear the regret in Dean’s voice and all of his previous anger drained out of him. He didn’t need to hear a full-blown apology to know that Dean was sorry. Castiel could see it in his eyes. He could feel it in the wobble of Dean’s bottom lip as more tears started to fall. Maybe it made him stupid or gullible to forgive Dean just like that, but at the end of the day he just wanted his friend back. 

Castiel didn’t pick his best friends because they were convenient. He picked them because he could tell, instinctively, that they were good people. He saw it in Dean three and a half years ago and he could still see it now. 

And Castiel couldn’t imagine living with himself if he didn’t trust his gut when he knew Dean was sorry for what happened between them. 

“Then stop pushing me away now,” he told the taller man. 

Dean’s eyes widened. “I’m trying,” he professed. “I’ve been trying to talk to you more to… to say how sorry I am for what I did and how badly I hurt—” 

“I forgive you.”

The words were past his lips before Dean could finish apologizing. 

But Dean didn’t seem willing to accept it. 

“You shouldn’t,” he declared with a stubborn headshake but Cas wasn’t about to change his mind. His mind was made up and now that the words were already spoken, he refused to take them back. Dean was meant to be his best friend, he wasn’t just going to throw that away, not if he could help it. 

“Well I do anyway.” 

Something must’ve crumbled inside Dean because he choked back a sob. 

“I never wanted to hurt you,” he cried into his fist. “I really didn’t, Cas. I wanted to be the person who made you happy.” 

“You did,” Cas insisted easily. He’s not sure he’d ever been as happy as he was when he and Dean were together. It’s why it devastated him so much to lose it. 

“I’m sorry I’m like this,” Dean continued, stuttering over his words. “It just happens sometimes and I’m probably always going to be like this. It doesn’t just disappear forever.” 

His heart ached for his friend who thought he was so broken when Castiel knew Dean was anything but. Castiel could see how much Dean hated struggling with this. There was no doubt in his mind that Dean thought he _deserved_ to struggle with this but it couldn’t be further from the truth. Cas knew he couldn’t take away Dean’s pain but he’d do whatever he could to help ease it a little. 

“That’s okay,” Cas promised. “It doesn’t have to disappear forever but I want to be there to help when you need it.” 

Another sob was stifled by Dean’s fist. “I miss you,” he cried. 

He didn’t fight himself this time when the urge to hug Dean overcame him. He rushed across the room and pulled his weeping friend into a crushing hug. 

“I miss you too,” he whispered against Dean’s neck, melting into the way Dean’s arms squeezed tighter around his waist. 

Cas held him tight, letting Dean know it was okay—that they were okay, until his friend started to get his breathing under control. 

When they pulled back from the hug, Dean’s green eyes were vibrant against the red, his cheeks were blotchy, but he still looked so gorgeous, Cas could melt. 

He loved Dean, even still, and he couldn’t imagine himself ever stopping. But not knowing where they stood or if Dean was ready for anything more, Castiel asked, “Can we… can we please be friends again?” 

At first Dean looked at him relieved before his eyes became sad again. He shook his head. 

“No. I don’t wanna be your friend Cas,” he stated plainly, crushing Castiel completely. 

He stumbled back quickly but didn’t get far before Dean caught his hands in his. 

“I wanna be _with_ you. For real. I want to be your boyfriend and get kiss you and do all the things we never did like go out on real dates and hold hands when we’re walking next to each other and tell all our friends that we’re _really_ fucking good together. If you want to just be friends, I’ll try, but I don’t think I’ll be able to do it.” 

For a moment, he felt like he was dreaming. Only in his wildest dreams did he ever hear Dean say such things. Words he’d wanted for months, _I wanna be with you,_ were now _his._ He could have this and he almost couldn’t breathe with how much it meant to him. 

He wanted to say everything, to shout his love, but his mind and mouth couldn’t sync up and what came out of his mouth wasn’t what he’d planned to say. 

“You can kiss me now.” 

Dean’s jaw dropped and the faintest smile crossed his lips. 

“What?” he asked. And Castiel could tell Dean was hoping to hear the words too. 

It was that tender hope that had Cas forming a coherent thought. 

“I want all that too. I want to be with you. So can you kiss me now?” 

Before Castiel could even blink Dean was moving towards him, and Castiel was drawn in like the tide, crashing into him halfway as their lips knocked together in a bruising kiss. The warmth of Dean’s broad palms against the sides of his face, the sturdiness of Dean’s body against him as Castiel wrapped his arms desperately around the other man—it was surreal. He’d never been kissed like this in his life. He could feel it all the way down his spin, to his toes, how deeply they’d both wanted this. 

He wholeheartedly believed they were made for each other. There was no other plausible explanation how a first kiss could feel so engraved in their being, as comfortable and familiar as if they’d shared it for years. 

He could feel himself glowing as they pulled back and smiled. 

“Can I hold you tonight?” Dean’s words were breathless and shy and Castiel could only answer them with an affirmative kiss. He took his man by the hand and led them over to Dean’s bed before crawling into his spot and opening his arms. 

It had been so long since they’d been there, laying in the small confines of Dean’s bed with their arms around each other but it was like falling back into place. The scent of Dean surrounding him, the strength of Dean’s arms as he tugged Cas’s body against his own to deepen their kisses, it stirred the want inside Cas’s core that had never gone away for this man. 

He pulled Dean further into the kiss until he could roll onto his back, taking Dean with him. His legs widened as Dean slotted in between them, pajamas and boxers the only barrier between them. 

“Cas,” Dean panted against his lips before moving to kiss his jawline. 

He whispered it again against the chords of his neck. 

“Cas,” he said once more as his lips found the collar of Castiel’s t-shirt. 

Cas’s fingers threaded through Dean’s hair, tugging enough to get those perfect lips back on his, but Dean pulled back, just before their lips could meet. 

“Just this tonight,” he whispered, stroking a few pieces of hair off of Cas’s forehead. “You have no idea how badly I want you but I just want to kiss you and hold you tonight. Make up for all the time I never got to before.” 

Cas traced his thumb across the rough stubble at Dean’s jawline and melted a little when Dean’s lips moved to kiss the tip of his thumb. Just that tiny gesture was enough to make Castiel’s heart grow double in size and he wasn’t sure his heart could take it. The happiness coursing through him could easily fill the moon. 

“Then why aren’t we kissing right now?” He asked with a smirk and wasn’t disappointed when Dean kissed it right off. 

It was well into dawn by the time their kisses slowed down. Castiel had convinced Dean to at least take off their shirts in order to sleep but neither one of them seemed willing to be the first one to close their eyes. 

Dean’s fingers were tracing delicate patterns all over Cas’s skin and Cas couldn’t get his fingers out of Dean’s hair. 

“I’m glad I came home tonight,” Cas whispered between them. 

“Me too.”

The dreamy quality to Dean’s voice could almost lull Cas to sleep. He smiled against the pillow knowing he’d get to hear that voice for a long, long time. 

“I almost went back to Hannah’s after leaving Aaron’s,” Cas added with a small huff of laughter, “but I guess the universe needed me here.” 

“Aaron?” Dean asked with a frown. 

“The guy… from last night.” 

Cas watched Dean try to hide a grimace and he immediately felt like a fool. 

“Oh, no. I’m sorry!” He said quickly. “I shouldn’t have even mentioned that.” 

Broad hands swept up his back, pulling him in. 

“It’s okay, Cas.” 

“No. We’re here and we’re good and I shouldn’t have said—” 

A kiss cut him off, and Cas relaxed into Dean’s hold. 

“Baby, it’s okay. I’m not upset.” The softness in Dean’s eyes held complete truth and Cas sank into another, longer kiss. He’d already grown to love the taste of Dean’s tongue against his own and couldn’t imagine having not known it until this night. 

As they pulled back from this kiss, Dean’s eyes were set on Cas’s and he could tell his boyfriend had something he wanted to get off his chest. 

“Even if you and him did anything,” Dean began, “even if you slept with him... it would’ve been okay. I mean I would have been jealous but it’d be okay. I wouldn’t have been upset.”

“No it wouldn’t,” Cas disagreed. 

“It wouldn’t have changed how I feel. You can sleep with—”

He understood where Dean was coming from and it made him so proud to know he was with such a tender and caring man, but Castiel cut him off to explain his own heart. 

“It wouldn’t have been okay with me,” he confessed. “I thought at the start of this all that I wouldn’t care about sex and being with whoever but… being with you, knowing you’re the only man I’ve ever been with, who has ever seen me or touched me that way... it’s special to me. It means something to me. And maybe we don’t end up together but for now I want it to only be you. Right now, I want to only ever be yours.”

He could tell his words overwhelmed Dean as his face turned up in emotion and he grabbed for Cas’s hand, pulling it to his mouth and kissing it before tugging it tightly against his chest. Never in his life had Castiel ever seen so much fire and passion in someone’s eyes as he did in that moment with Dean looking at him. 

“You know I’m only yours too?” Dean asked, waiting for Cas to nod. When he was satisfied Castiel meant it, his words continued and Cas isn’t sure if he could’ve ever been prepared for them. “I’ve never—I’ve never loved anyone romantically. I didn’t even think I could love anyone, not in the way they deserved, but I love you more than I knew was possible and I’ll only ever love you like this.” 

He was completely speechless from the confession, his heart absolutely consumed with elation. 

“Dean…” 

“It’s okay if you don’t feel that way too,” Dean rushed to add, “but I just wanted to tell you—” 

“I love you so much,” Castiel breathed. He pressed their foreheads together, inhaling Dean’s trembling breaths before he placed one more kiss against his best friends’ lips, sealing the promise between them. 

“We’re really together?” Dean asked in disbelief. 

“We really are.” 

“Good,” Dean smiled radiantly. He looked so undeniably happy and left Castiel no room to doubt how much Dean loved him. It took his breath away to know he found his person. They were young, but somehow he just _knew._

“You know what I’m really excited about?” Dean asked suddenly, pulling Cas from his thoughts. 

“Hmm?” 

“Holding your hand at breakfast tomorrow,” he said with a kiss. “Kissing you across the table.” He kissed Cas again and again, punctuating each sentence with it. “Pulling you into a hug whenever I feel like it—Hearing you say you love me too.” 

“I can’t wait,” he whispered against Dean’s smile. 

As for Castiel? He was excited for all of their forever.

**Notes for the Chapter:**

> So? Are we happy? Was it worth the wait? 
> 
> I cannot believe I spent about two and a half years writing this story. I was reminiscing tonight and realized I'd started toying with the idea as I was writing Sleep Without You and asked myself "what if I did a best friend story with the all cuddles but make it smutty?" It was just a little bit of fun in between writing my other stories since I was still really new to fanfiction and didn't think many people who really read my work. MAN was I wrong. THANK YOU for reading this story or any of my other works. The comments you all leave me actually brighten my day and sometimes bring me to tears because of how kind you all are. I'm still so blown away any of you would read this stuff. 
> 
> ANYWAY before I get blubbery, I really hope you liked this story. BUT It's not done here. There will be another part! My plan is for it to be a pretty lengthy timestamp but since these boys don't like sticking with my plans, who knows where it can go. 
> 
> Thank you all again. I appreciate you so much.   
<3 Paige

**Author's Note:**

> If you liked this, I also wrote these: 
> 
> Friends to lovers:   
[Sleep Without You](https://archiveofourown.org/works/10775289/chapters/23899212)   
[There Goes My Life](https://archiveofourown.org/works/12011787/chapters/27182904)   
[Alright](https://archiveofourown.org/works/11589315/chapters/26046594)
> 
> Angst:   
[He Didn’t Have to Be Series](https://archiveofourown.org/series/766410)   
[Don’t You Wanna Stay](https://archiveofourown.org/works/10634991)
> 
> Nearest and dearest to my heart:   
[Highway 20 Ride](https://archiveofourown.org/works/21317785/chapters/50767201)


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